Name: 498-07-7|(1R,2S,3S,4R,5R)-6,8-Dioxabicyclo[3.2.1]octane-2,3,4-triol|98%
Brand: Ambeed
SKU: A380273
Price: 6.0 USD
Availability: InStock
Rating: 97 (28 reviews)

1
[ 492-61-5 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	Erhitzen im Vakuum;
	With pyridine; p-toluenesulfonyl chloride for 1.5h;
	beim Erhitzen;

	Multi-step reaction with 3 steps 1: 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine / water / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 2: 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 3: sodium hydroxide / water / pH 7 / Inert atmosphere; Schlenk technique
	With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine at 0 - 5℃; for 0.5h;	1 Preparation of Compounds of Formula 6 D-glucose 45g, water 1800ml, and triethylamine 303.6g were added to the reaction flask.Stir, cool to 0-5°C, add 2-chloro-1, 3-dimethylimidazolium hydrochloride 170.1g in batches, control the reaction at 0-5°C for 30 minutes after adding,The reaction solution was concentrated to dryness under reduced pressure, 400 ml of acetonitrile was added, and the mixture was stirred for 1 hour and filtered. The filter cake was washed with 100 ml of acetonitrile. The filtrate was combined and concentrated under reduced pressure to give the compound of Formula 6, which was used for the next step;

Reference： [1]Karrer [Helvetica Chimica Acta, 1920, vol. 3, p. 258]
[2]Bourke, David G.; Collins, David J.; Hibberd, Angus I.; McLeod, Malcolm D. [Australian Journal of Chemistry, 1996, vol. 49, # 3, p. 425 - 434]
[3]Karrer [Helvetica Chimica Acta, 1920, vol. 3, p. 258] Picon [Bulletin de la Societe Chimique de France, 1953, p. 681,682,684] Golowa et al. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 389;engl.Ausg.S.399]
[4]Alexander; Lim; Amso; Brimble; Fairbanks [Organic and Biomolecular Chemistry, 2017, vol. 15, # 10, p. 2152 - 2156]
[5]Current Patent Assignee: JIANGSU MEIDIKE CHEMICALS - CN107686495, 2018, A Location in patent: Paragraph 0033; 0066-0068

2
[ 108-24-7 ]
[ 498-07-7 ]
[ 13242-55-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 20℃; for 0.2h;
62%	With pyridine at 20℃; for 3h;
	With pyridine

	With sodium acetate
	Yield given;
	With pyridine Yield given;
	With pyridine Ambient temperature;
	With sodium acetate at 100℃; for 1h; Yield given;
	With dmap In ethyl acetate Yield given;
	With pyridine for 4h; Yield given;

Reference： [1]Lee, Jinq-Chyi; Tai, Cheng-An; Hung, Shang-Cheng [Tetrahedron Letters, 2002, vol. 43, # 5, p. 851 - 855]
[2]Kloosterman, M.; Dees, M. J.; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, p. 116 - 119]
[3]Tanaka [Memoirs of the College of Science, Kyoto Imperial University, 1930, vol. <A> 13, p. 239,251] Hurd; Cantor [Journal of the American Chemical Society, 1938, vol. 60, p. 2677,2679] Karrer; Kamienski [Helvetica Chimica Acta, 1932, vol. 15, p. 739,744] Budesinsky, Milos; Polakova, Jana; Hamernikova, Michaela; Cisarova, Ivana; Trnka, Tomas; Cerny, Miloslav [Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 3, p. 311 - 336]
[4]Zemplen; Gerecs [Chemische Berichte, 1931, vol. 64, p. 1545,1550]
[5]Takeda, Yasuko; Akimoto, Toshio; Kyogoku, Yoshimasa [Carbohydrate Research, 1982, vol. 106, p. 175 - 192]
[6]Lafont, Dominique; Boullanger, Paul; Cadas, Olivier; Descotes, Gerard [Synthesis, 1989, # 3, p. 191 - 194]
[7]Goodwin, James C. [Carbohydrate Research, 1985, vol. 143, p. 61 - 68]
[8]Wisniewski, Andrzej; Madaj, Janusz; Skorupowa, Eugenia; Sokolowski, Janusz [Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 873 - 880]
[9]Zottola, Mark A.; Alonso, Ricardo; Vite, Gregory D.; Fraser-Reid, Bert [Journal of Organic Chemistry, 1989, vol. 54, # 26, p. 6123 - 6125]
[10]Bourke, David G.; Collins, David J.; Hibberd, Angus I.; McLeod, Malcolm D. [Australian Journal of Chemistry, 1996, vol. 49, # 3, p. 425 - 434]

3
[ 98-88-4 ]
[ 498-07-7 ]
[ 23567-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; chloroform
	With pyridine
	With pyridine In toluene at 70℃; for 8h;

	With pyridine In toluene at 70℃; for 7h;
	With pyridine
265 g	With pyridine; dmap In dichloromethane at 0 - 20℃; for 3h;	1 Preparation of Phenyl-6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-L-idopyranoside Modified and Optimized Procedure l,6-anhydro-3-O-benzyl- -L-idopyranose (150g, 0.6 mol) was dissolved in the mixture EtOAc/MeOH (1 : 1, 1200 ml) and hydrogenated over 10% Pd/C (15 g) at 50 °C, 5 atm for 4h. The mixture was cooled to 20 °C, filtered through Celite and evaporated under reduced pressure. The oily residue and DMAP (22 g, 0.18 mol) were dissolved in CH2C12 (400 ml) and Pyridine (404 ml, 5.0 mol) and the resulted mixture was cooled to 0 °C. Benzoyl chloride (276 g, 229 ml, 1.96 mol) was slowly added and the reaction was stirred for 3h at 20 °C (TLC monitoring). The volatiles were evaporated under reduced pressure and the solid residue was portioned between EtOAc (2L) and water (2L). The phases were separated, the organic one was washed with cold 2N aqueous HC1 (700 ml), water (500ml) and 10% aqueous NaHC03 (500 ml), dried over Na2S04, filtered and concentrated under reduced pressure to give ~300g of solid residue. The residue was crystallized from Isopropanol afforded 265g (94%) yield) of the desired tribenzoate as white solid.

Reference： [1]Csueroes et al. [Acta Chimica Academiae Scientiarum Hungaricae, 1959, vol. 21, p. 169,176]
[2]Bergmann; Koch [Chemische Berichte, 1929, vol. 62, p. 311]
[3]Gómez, Ana M.; Moreno, Eduardo; Valverde, Serafín; López, J.Cristóbal [Tetrahedron Letters, 2002, vol. 43, # 32, p. 5545 - 5549]
[4]Yi, Yuetao; Zhou, Zhongxuan; Ning, Jun; Kong, Fanzuo; Li, Jianqiang [Synthesis, 2003, # 4, p. 491 - 496]
[5]Location in patent: scheme or table Liu, Hongmei; Cheng, Shuihong; Liu, Jun; Du, Yuguang; Bai, Zhihui; Du, Yuguo [Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 14, p. 5634 - 5638]
[6]Current Patent Assignee: OPKO HEALTH INC - WO2018/35050, 2018, A1 Location in patent: Paragraph 0073

4
[ 498-07-7 ]
[ 74-88-4 ]
[ 2951-86-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide Inert atmosphere;
	With methanol; silver(l) oxide
	With dimethylsulfide; silver(l) oxide In water; acetonitrile for 24h;

Reference： [1]Fu, Liye; Li, Lingyao; Wang, Jun; Knickelbein, Kyle; Zhang, Lin; Milligan, Ian; Xu, Yi; O'Hara, Kylie; Bitterman, Lindsay; Du, Wenjun [Chemical Communications, 2014, vol. 50, # 84, p. 12742 - 12745]
[2]Irvine; Oldham [Journal of the Chemical Society, 1921, vol. 119, p. 1744,1753]
[3]Lehmann, Marco M.; Fischer, Maria; Blees, Jan; Zech, Michael; Siegwolf, Rolf T. W.; Saurer, Matthias [Rapid Communications in Mass Spectrometry, 2016, vol. 30, # 1, p. 221 - 229]

5
[ 1464-44-4 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium hydroxide In water for 9h; Heating;
	With potassium hydroxide

Reference： [1]Baker, Raymond; Boyes, R. Hugh O.; Broom, D. Mark P.; O'Mahony, Mary J.; Swain, Christopher J. [Journal of the Chemical Society. Perkin transactions I, 1987, p. 1613 - 1622]
[2]Montgomery et al. [Journal of the American Chemical Society, 1943, vol. 65, p. 3,6]
[3]Takeda, Yasuko; Akimoto, Toshio; Kyogoku, Yoshimasa [Carbohydrate Research, 1982, vol. 106, p. 175 - 192]

6
[ 10416-59-8 ]
[ 498-07-7 ]
[ 7449-14-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrabutyl ammonium fluoride In tetrahydrofuran for 16h; Ambient temperature;

Reference： [1]Johnson [Carbohydrate Research, 1992, vol. 237, # 1, p. 313 - 318]

7
[ 18312-45-3 ]
[ 498-07-7 ]
[ 93173-18-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	In pyridine at 30℃; for 48h; Candida antarctica lipase;

Reference： [1]Pulido; Gotor [Carbohydrate Research, 1994, vol. 252, p. 55 - 68]

8
[ 100-39-0 ]
[ 498-07-7 ]
[ 10548-46-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;
90%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;
86%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	1,6-Anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (5a). To a solution of levoglucosan (1 equiv., 5 g,30.5 mmol) in DMF (200 mL) at 0 °C was added benzyl bromide (3.5 equiv., 18.3 g, 12.8 mL, 106 mmol).Sodium hydride (60% in oil, 5 equiv., 6.11 g, 152 mmol) was added portionwise. The ice bath wasremoved, and the reaction was stirred overnight at r.t. Methanol (60 mL) was added, and 15 min later water was added (120 mL). The aqueous layer was extracted with EtOAc (3 200 mL), and thecombined organic extracts were washed with brine (1 x 200 mL). The organic solution was dried oversodium sulfate, filtered, concentrated to an oil that was purified by flash chromatography (PetroleumEther/EtOAc 8/2 to 6/4), to afford a solid that was then recrystallized from ethanol to afford 5a(11.34 g, 26.23 mmol) as white crystals in 86% yield. 1H NMR (300 MHz, CDCl3) δ (ppm) 7.35-7.22 (m,15H, Ph), 5.46 (s, 1H, H-1), 4.64-4.51 (m, 5H, H-5, O-CH2-Ph), 4.45 (d, J = 12.1 Hz, 1H, O-CH2-Ph) 4.41(d, J = 12.1 Hz, 1H, O-CH2-Ph), 3.91 (d, J = 7.2 Hz, 1H, H-6), 3.68 (t, J = 6.5 Hz, 1H, H-6), 3.59 (m, 1H,H-3), 3.35 (m, 2H, H-2, H-4). MS (ESI): m/z [M + K]+ calculated for [C27H28O5K]+: 471.16, found 471.16.The analyses are in good agreement with the experimental data reported in literature [20].

77%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide
77%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide Further stages.;
	With sodium hydride In N,N-dimethyl-formamide at 25℃;
	With sodium hydride 1.) DMF, from 0 deg C to RT; Multistep reaction;
	With sodium hydride 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h; Yield given. Multistep reaction;
	With sodium hydride In N,N-dimethyl-formamide
63.45 g	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide; mineral oil for 25h; Cooling with ice; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 15h; Cooling with ice; Inert atmosphere;

Reference： [1]Location in patent: experimental part Liu, Hongmei; Cheng, Shuihong; Liu, Jun; Du, Yuguang; Bai, Zhihui; Du, Yuguo [Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 14, p. 5634 - 5638]
[2]Bailliez, Vincent; Figueiredo, Renata M. de; Olesker, Alain; Cleophax, Jeannine [Tetrahedron Letters, 2003, vol. 44, # 51, p. 9151 - 9154]
[3]Céspedes Dávila, Maria F.; Schneider, Jérémy P.; Godard, Amélie; Hazelard, Damien; Compain, Philippe [Molecules, 2018, vol. 23, # 4]
[4]Fuerstner, Alois; Albert, Martin; Mlynarski, Jacek; Matheu, Maribel; DeClercq, Erik [Journal of the American Chemical Society, 2003, vol. 125, # 43, p. 13132 - 13142]
[5]Fuerstner, Alois; Albert, Martin; Mlynarski, Jacek; Matheu, Maribel [Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1168 - 1169]
[6]Nambiar, Sudhir; Daeuble, John F.; Doyle, Ronald J.; Taylor, K. Grant [Tetrahedron Letters, 1989, vol. 30, # 17, p. 2179 - 2182]
[7]Panek, James S.; Sparks, Michelle A. [Journal of Organic Chemistry, 1989, vol. 54, # 9, p. 2034 - 2038]
[8]McDevitt, Jason P.; Lansbury Jr., Peter T. [Journal of the American Chemical Society, 1996, vol. 118, # 16, p. 3818 - 3828]
[9]Egusa, Kenji; Fukase, Koichi; Nakai, Yoshihiko; Kusumoto, Shoichi [Synlett, 2000, # 1, p. 27 - 32]
[10]Hager, Dominik; Paulitz, Christian; Tiebes, Joerg; Mayer, Peter; Trauner, Dirk [Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10784 - 10801]

9
[ 133360-56-2 ]
[ 498-07-7 ]
[ 118315-57-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	In pyridine at 30℃; for 48h; Candida antarctica lipase;

Reference： [1]Pulido; Gotor [Carbohydrate Research, 1994, vol. 252, p. 55 - 68]

10
[ 100-44-7 ]
[ 498-07-7 ]
[ 10548-46-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; potassium carbonate In dimethyl sulfoxide; benzene for 5h; Ambient temperature;
77%	With potassium hydroxide In dimethyl sulfoxide for 2h; Ambient temperature;
65%

Reference： [1]Szeja, W.; Fokt, I.; Grynkiewicz, G. [Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 6, p. 224 - 226]
[2]Kovac, Pavol; Lerner, Laura [Carbohydrate Research, 1988, vol. 184, p. 87 - 112]
[3]Ledford, Brian E.; Carreira, Erick M. [Journal of the American Chemical Society, 1995, vol. 117, # 47, p. 11811 - 11812]

11
[ 98-59-9 ]
[ 498-07-7 ]
[ 20204-80-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In pyridine; chloroform at 25℃; for 50h;
83%	With pyridine In dichloromethane at 0℃; for 20h; Inert atmosphere;
80%	With pyridine In chloroform at 0 - 20℃; for 18h;

71%	With pyridine In acetone at 0℃; for 2h;
	In pyridine; acetone
45.64 g	With pyridine In chloroform at 20℃; Inert atmosphere; Cooling;
	With pyridine In chloroform at 0 - 20℃; for 18h; Inert atmosphere;
	With pyridine In chloroform at 0 - 20℃; for 16h;
	With pyridine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; regioselective reaction;	1,6:3,4-Dianhydro-2-O-p-tolylsulfonyl-β-D-galactopyranose (2) Prepared from a literature procedure [1]. To a cooled (0 °C) solution of levoglucosan (1, 6.00 g, 37.0 mmol) indry pyridine (30 mL) was added a cooled solution of p-toluenesulfonyl chloride (15.0 g, 79.0 mmol) in 1:1pyridine/dichloromethane (60 mL). The reaction mixture was allowed to reach ambient temperature and wasstirred for 12 hours. The reaction mixture was quenched with methanol (10 mL) and concentrated in vacuo. Theresidue was dissolved in dry pyridine (2.4 mL) and a solution of sodium methoxide in methanol (0.6 M, 100 mL)was added dropwise during 3 hours. After 11 hours the reaction concluded with the precipitation of a white solidthat corresponded to compound 2. This compound was isolated by filtration to afford 2 (8.05 g, 27.0 mmol, 73%)as a white solid.

Reference： [1]Fox; Hiner; Warrier; White [Tetrahedron Letters, 1988, vol. 29, # 24, p. 2923 - 2926]
[2]St-Gelais, Jacob; Côté, Émilie; Lainé, Danny; Johnson, Paul A.; Giguère, Denis [Chemistry - A European Journal, 2020, vol. 26, # 59, p. 13499 - 13506]
[3]Troup, Robert I.; Jeffries, Benjamin; Saudain, Raphael El-Bekri; Georgiou, Eleni; Fish, Johanna; Scott, James S.; Chiarparin, Elisabetta; Fallan, Charlene; Linclau, Bruno [Journal of Organic Chemistry, 2021, vol. 86, # 2, p. 1882 - 1900]
[4]Krohn, Karsten; Gehle, Dietmar; Floerke, Ulrich [European Journal of Organic Chemistry, 2005, # 13, p. 2841 - 2848]
[5]Baker, Raymond; Boyes, R. Hugh O.; Broom, D. Mark P.; Devlin, J. Alastair; Swain, Christopher J. [Journal of the Chemical Society. Chemical communications, 1983, # 15, p. 829 - 831]
[6]Rasmussen, Tina Secher; Jensen, Henrik Helligso [Organic and Biomolecular Chemistry, 2010, vol. 8, # 2, p. 433 - 441]
[7]Lainé, Danny; Denavit, Vincent; Giguère, Denis [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4986 - 4992]
[8]Denavit, Vincent; St-Gelais, Jacob; Tremblay, Thomas; Giguère, Denis [Chemistry - A European Journal, 2019, vol. 25, # 39, p. 9272 - 9279]
[9]Holmstrøm, Thomas; Pedersen, Christian Marcus; Raydan, Daniel [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 2788 - 2794]

12
[ 1005-56-7 ]
[ 498-07-7 ]
[ 141810-56-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine In acetonitrile for 2h; Ambient temperature;

Reference： [1]Barton, Derek H. R.; Jang, Doo Ok; Jaszberenyi, Joseph Cs. [Tetrahedron, 1993, vol. 49, # 33, p. 7193 - 7214]
[2]Barton, Derek H. R.; Jang, Doo Ok; Jaszberenyi, Joseph Cs. [Tetrahedron Letters, 1992, vol. 33, # 44, p. 6629 - 6632]

13
[ 498-07-7 ]
[ 6167-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; 2-methoxy-ethanol; potassium carbonate; p-toluenesulfonyl chloride 1.) benzene, methyl sulfoxyde, 10 min.; 2.) 20 min.; Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: pyridine / 48 h / 25 °C 2: NaOMe, MeOH / CHCl₃ / 0.5 h / 0 °C
	Multi-step reaction with 2 steps 1: pyridine / chloroform / 18 h / 0 - 20 °C / Inert atmosphere 2: sodium methylate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: pyridine / chloroform / 16 h / 0 - 20 °C 2: sodium methylate / dichloromethane; methanol / 1 h / 0 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: pyridine; sodium methylate / methanol / 3 h / Inert atmosphere

Reference： [1]Hodges, Paul J.; Procter, Garry [Tetrahedron Letters, 1985, vol. 26, # 34, p. 4111 - 4114]
[2]Szeja, Wieslaw [Carbohydrate Research, 1988, vol. 183, p. 135 - 139]
[3]Nakata; Akiyama; Kamata -i.; Kojima; Masuda Kinoshita; Tatsuta [Tetrahedron, 1990, vol. 46, # 13-14, p. 4629 - 4652]
[4]Lainé, Danny; Denavit, Vincent; Giguère, Denis [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4986 - 4992]
[5]Denavit, Vincent; St-Gelais, Jacob; Tremblay, Thomas; Giguère, Denis [Chemistry - A European Journal, 2019, vol. 25, # 39, p. 9272 - 9279]
[6]Holmstrøm, Thomas; Pedersen, Christian Marcus; Raydan, Daniel [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 2788 - 2794]

14
[ 2280-44-6 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In water-d2 at 0℃; for 0.25h;
99%	With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In water-d2 at 0℃; for 0.25h;
32%	With Amberlyst-15 In N,N-dimethyl-formamide at 99.84℃; for 3h;

	With pyridine; sodium hydroxide; p-toluenesulfonyl chloride 1.) from 18 deg C to 22 deg C, 30 min, 2.) 60 min; Multistep reaction;
	Multi-step reaction with 2 steps 1: pyridine / 1 h / 0 °C 2: NaOH / H₂O / 1 h / pH=10
	With pyridine; p-toluenesulfonyl chloride at 15 - 20℃; for 1.5h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: triethylamine; Sodium thiosulfate pentahydrate; 2-chloro-1,3-dimethylimidazolinium chloride / water-d2; acetonitrile / 1.5 h / 0 °C 2: potassium hydroxide / water-d2 / 13 h / 20 °C
	Multi-step reaction with 2 steps 1: 2-chloro-1,3-dimethylimidazolinium chloride; sodium thiosulfate; triethylamine / acetonitrile; water-d2 / 1.5 h / 0 °C 2: potassium hydroxide / water-d2

Reference： [1]Tanaka, Tomonari; Huang, Wei Chun; Noguchi, Masato; Kobayashi, Atsushi; Shoda, Shin-ichiro [Tetrahedron Letters, 2009, vol. 50, # 18, p. 2154 - 2157]
[2]Fairbanks, Antony J. [Carbohydrate Research, 2021, vol. 499]
[3]Takagaki, Atsushi; Ohara, Mika; Nishimura, Shun; Ebitani, Kohki [Chemical Communications, 2009, # 41, p. 6276 - 6278]
[4]Zottola, Mark A.; Alonso, Ricardo; Vite, Gregory D.; Fraser-Reid, Bert [Journal of Organic Chemistry, 1989, vol. 54, # 26, p. 6123 - 6125]
[5]Kloosterman, M.; Dees, M. J.; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, p. 116 - 119]
[6]Hager, Dominik; Paulitz, Christian; Tiebes, Joerg; Mayer, Peter; Trauner, Dirk [Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10784 - 10801]
[7]Meguro, Yasuhiro; Noguchi, Masato; Li, Gefei; Shoda, Shin-Ichiro [Organic Letters, 2018, vol. 20, # 1, p. 76 - 79]
[8]Fairbanks, Antony J. [Carbohydrate Research, 2021, vol. 499]

15
[ 4468-72-8 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide In water for 120h; Heating;

Reference： [1]Boissière-Junot, Nathalie; Tellier, Charles; Rabiller, Claude [Journal of Carbohydrate Chemistry, 1998, vol. 17, # 1, p. 99 - 115]

16
[ 98799-41-8 ]
[ 498-07-7 ]
1,6-anhydro-2,3,4-tris-O-(2-iodo-3,4,5-trimethoxybenzoyl)-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;

Reference： [1]Dai, Dongcheng; Martin, Olivier R. [Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7628 - 7633]

17
[ 994-30-9 ]
[ 498-07-7 ]
[ 220277-30-5 ]
1,6-anhydro-2,3,4-tris-O-(triethylsilyl)-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 90% 2: 7%	With pyridine In dichloromethane for 0.416667h;

Reference： [1]Ernst, Alexander; Schweizer, W. Bernd; Vasella, Andrea [Helvetica Chimica Acta, 1998, vol. 81, # 12, p. 2157 - 2189]

Yield	Reaction Conditions	Operation in experiment
18.5%	In solid at 350 - 450℃;
	Erhitzen im Vakuum;

19
[ 98-59-9 ]
[ 498-07-7 ]
[ 20204-80-2 ]
[ 50880-93-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 14%	With pyridine at -5℃; for 12.5h;

Reference： [1]Belyk, Kevin M.; Leonard Jr., William R.; Bender, Dean R.; Hughes, David L. [Journal of Organic Chemistry, 2000, vol. 65, # 8, p. 2588 - 2590]

20
forest plant material [ No CAS ]
[ 93-51-6 ]
[ 2785-89-9 ]
[ 90-05-1 ]
[ 498-07-7 ]

Reference： [1]Chemosphere,2000,vol. 41,p. 735 - 741

21
[ 180675-80-3 ]
[ 498-07-7 ]
[ 365235-89-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 2,6-dimethylpyridine In 1,2-dichloro-ethane at 23℃; for 2.5h;

Reference： [1]Hoffmann, Barbara; Zanini, Diana; Ripoche, Isabelle; Buerli, Roland; Vasella, Andrea [Helvetica Chimica Acta, 2001, vol. 84, # 6, p. 1862 - 1888]

22
[ 108-24-7 ]
[ 498-07-7 ]
D-glucose pentaacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	at 20℃; for 5h;

Reference： [1]Lee, Jinq-Chyi; Tai, Cheng-An; Hung, Shang-Cheng [Tetrahedron Letters, 2002, vol. 43, # 5, p. 851 - 855]

23
[ 498-07-7 ]
[ 789-25-3 ]
2,4-O-bis(triphenylsilyl)-1,6-anhydro-D-glucose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With Proton Sponge; N,N-dimethyl acetamide at 60℃;

Reference： [1]Chung, Mee-Kyung; Orlova, Galina; Goddard, John D.; Schlaf, Marcel; Harris, Robert; Beveridge, Terrance J.; White, Gisele; Hallett, F. Ross [Journal of the American Chemical Society, 2002, vol. 124, # 35, p. 10508 - 10518]

24
[ 29681-57-0 ]
[ 498-07-7 ]
1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose [ No CAS ]
2,3-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-glucose [ No CAS ]
3,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-glucose [ No CAS ]
1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 22% 3: 11% 4: 6%	With [Rh(COD)(PPh₃)2]SbF₆ In N,N-dimethyl acetamide at 70℃;

Reference： [1]Chung, Mee-Kyung; Schlaf, Marcel [Journal of the American Chemical Society, 2005, vol. 127, # 51, p. 18085 - 18092]

25
[ 29681-57-0 ]
[ 498-07-7 ]
1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 84% 2: 15%	With [Ir(COD)(PPh₃)2]SbF₆ In N,N-dimethyl acetamide at 70℃;

Reference： [1]Chung, Mee-Kyung; Schlaf, Marcel [Journal of the American Chemical Society, 2005, vol. 127, # 51, p. 18085 - 18092]

26
(E)-3,4-di-O-acetylcaffeoyl chloride [ No CAS ]
[ 498-07-7 ]
[ 861897-18-9 ]

Yield	Reaction Conditions	Operation in experiment
57%	With pyridine In toluene at 20℃; for 8h;

Reference： [1]Saito, Shizuka; Kurakane, Satoshi; Seki, Miyuki; Takai, Eiji; Kasai, Takanori; Kawabata, Jun [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 13, p. 4191 - 4199]

27
[ 498-07-7 ]
polymer, M_w 33000 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 150℃; for 0.666667h;

Reference： [1]Satoh, Toshifumi; Imai, Tomoko; Ishihara, Hiroyuki; Maeda, Takahiro; Kitajyo, Yoshikazu; Sakai, Yoko; Kaga, Harumi; Kaneko, Noriaki; Ishii, Fumiaki; Kakuchi, Toyoji [Macromolecules, 2005, vol. 38, # 10, p. 4202 - 4210]

28
[ 498-07-7 ]
polymer, M_w 24500 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.9%	With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 130℃; for 0.333333h;

Reference： [1]Satoh, Toshifumi; Imai, Tomoko; Ishihara, Hiroyuki; Maeda, Takahiro; Kitajyo, Yoshikazu; Sakai, Yoko; Kaga, Harumi; Kaneko, Noriaki; Ishii, Fumiaki; Kakuchi, Toyoji [Macromolecules, 2005, vol. 38, # 10, p. 4202 - 4210]

29
[ 498-07-7 ]
polymer, M_w 62000 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.1%	With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 130℃; for 0.666667h;

Reference： [1]Satoh, Toshifumi; Imai, Tomoko; Ishihara, Hiroyuki; Maeda, Takahiro; Kitajyo, Yoshikazu; Sakai, Yoko; Kaga, Harumi; Kaneko, Noriaki; Ishii, Fumiaki; Kakuchi, Toyoji [Macromolecules, 2005, vol. 38, # 10, p. 4202 - 4210]

30
[ 498-07-7 ]
polymer, M_w 70600 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.8%	With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 150℃; for 0.666667h;

Reference： [1]Satoh, Toshifumi; Imai, Tomoko; Ishihara, Hiroyuki; Maeda, Takahiro; Kitajyo, Yoshikazu; Sakai, Yoko; Kaga, Harumi; Kaneko, Noriaki; Ishii, Fumiaki; Kakuchi, Toyoji [Macromolecules, 2005, vol. 38, # 10, p. 4202 - 4210]

31
[ 498-07-7 ]
polymer, M_w 49000 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 210℃;

Reference： [1]Satoh, Toshifumi; Imai, Tomoko; Ishihara, Hiroyuki; Maeda, Takahiro; Kitajyo, Yoshikazu; Sakai, Yoko; Kaga, Harumi; Kaneko, Noriaki; Ishii, Fumiaki; Kakuchi, Toyoji [Macromolecules, 2005, vol. 38, # 10, p. 4202 - 4210]

32
[ 498-07-7 ]
[ 497226-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h 2: trimethylsilyl triflate (TMSOTf) / acetonitrile / 16 h

Reference： [1]McDevitt, Jason P.; Lansbury Jr., Peter T. [Journal of the American Chemical Society, 1996, vol. 118, # 16, p. 3818 - 3828]

33
[ 498-07-7 ]
[ 82614-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h 2: 38 percent / trimethylsilyl triflate (TMSOTf) / acetonitrile / 16 h
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 25 h / Cooling with ice; Inert atmosphere 1.2: 15 h / 20 °C / Cooling with ice; Inert atmosphere 2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C / Inert atmosphere

Reference： [1]McDevitt, Jason P.; Lansbury Jr., Peter T. [Journal of the American Chemical Society, 1996, vol. 118, # 16, p. 3818 - 3828]
[2]Hager, Dominik; Paulitz, Christian; Tiebes, Joerg; Mayer, Peter; Trauner, Dirk [Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10784 - 10801]

34
[ 498-07-7 ]
[ 176257-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h 2: 38 percent / trimethylsilyl triflate (TMSOTf) / acetonitrile / 16 h 3: Et₃N / CH₂Cl₂ / 18 h 4: NaN₃ / dimethylformamide / 20 h / 90 °C

Reference： [1]McDevitt, Jason P.; Lansbury Jr., Peter T. [Journal of the American Chemical Society, 1996, vol. 118, # 16, p. 3818 - 3828]

35
[ 498-07-7 ]
Methanesulfonic acid (2R,3R,4R,5S,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h 2: 38 percent / trimethylsilyl triflate (TMSOTf) / acetonitrile / 16 h 3: Et₃N / CH₂Cl₂ / 18 h

Reference： [1]McDevitt, Jason P.; Lansbury Jr., Peter T. [Journal of the American Chemical Society, 1996, vol. 118, # 16, p. 3818 - 3828]

36
[ 498-07-7 ]
[ 132729-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 65 percent 2: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C 3: pyridine / dimethylformamide 4: HgO / diethyl ether; acetone 5: 40 percent / H₂ / PdOH/C / methanol / 760 Torr

Reference： [1]Ledford, Brian E.; Carreira, Erick M. [Journal of the American Chemical Society, 1995, vol. 117, # 47, p. 11811 - 11812]

37
[ 498-07-7 ]
[ 172909-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65 percent 2: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C

Reference： [1]Ledford, Brian E.; Carreira, Erick M. [Journal of the American Chemical Society, 1995, vol. 117, # 47, p. 11811 - 11812]

38
[ 498-07-7 ]
[ 172909-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 65 percent 2: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C 3: pyridine / dimethylformamide 4: HgO / diethyl ether; acetone

Reference： [1]Ledford, Brian E.; Carreira, Erick M. [Journal of the American Chemical Society, 1995, vol. 117, # 47, p. 11811 - 11812]

39
[ 498-07-7 ]
[ 172909-55-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 65 percent 2: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C 3: pyridine / dimethylformamide

Reference： [1]Ledford, Brian E.; Carreira, Erick M. [Journal of the American Chemical Society, 1995, vol. 117, # 47, p. 11811 - 11812]

40
[ 498-07-7 ]
Carbonic acid ethyl ester 3-[(2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, from 0 deg C to RT 2: 50 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 16 h / from 0 deg C to RT 3: imidazol 4: H₂ / 10percent Pd/C / methanol; pyridine / Ambient temperature

Reference： [1]Panek, James S.; Sparks, Michelle A. [Journal of Organic Chemistry, 1989, vol. 54, # 9, p. 2034 - 2038]

41
[ 498-07-7 ]
Carbonic acid ethyl ester 3-[(2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, from 0 deg C to RT 2: 50 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 16 h / from 0 deg C to RT 3: imidazol 4: H₂ / 10percent Pd/C / methanol; pyridine / Ambient temperature

Reference： [1]Panek, James S.; Sparks, Michelle A. [Journal of Organic Chemistry, 1989, vol. 54, # 9, p. 2034 - 2038]

42
[ 75-77-4 ]
[ 498-07-7 ]
[ 18395-35-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dichloromethane at -10 - 20℃; for 7 - 11h;	1 Synthesis of 2,4-di-trimethylsiloxanyl-1,6-anhydro-β-D-glucose (Compound 2) 81 g of (0.5 mol) Compound 1,100 ml anhydrous triethylamine and 2 g of N',N-dimethylamino pyridine were dissolved in 400 ml anhydrous dichloromethane. Temperature was lowered to -10° C. 120 g trichloromethyl silyl was added slowly to the solution and the temperature of the reacting mixed solution was controlled in the range between -10° C. and -5° C. After the dropping, the solution was stirred for 2-3 hr at -10° C.-5° C. and then continued the stirring for 5-8 hr. The course of the reaction was monitored by TLC. After the complete conversion of all raw materials, the reacting solution was poured into 2000 ml of water and stirred for 15 min. The organic phase was separated. The aqueous phase was extracted with dichloromethane for 3 times and the organic phase was combined with the former one. The combined organic phase was washed successively with appropriate amount of 1N HCl, water and saturated brine and then dried with anhydrous magnesium sulfate. Active carbon was added to decolor the dried solution. Filtered to give 150 g of Compound 2 (determined by HPLC, yield: 98%). Solvent in the solution did not need to distill off and the solution can be used to carry out the next reaction. A small amount of the solution was concentrated at 200° C. -230° C. by vacuum distillation (0.1 mm Hg) and a slightly pale yellow liquid was obtained with boiling point at 280° C.-285° C., [α]20D -32° (c 1.44, CHCl3), 1H NMR (300 Hz, CDCl), hydrogen proton of methyl at 2 and 4 position of Si: 0.08 ppm (-CH3 s peak), 1.9 ppm (-OH s peak), MS: 307 (M+).

Reference： [1]Current Patent Assignee: HANDE PHARMA - US2006/3963, 2006, A1 Location in patent: Page/Page column 4-5

43
[ 498-07-7 ]
[ 1012081-04-7 ]

Yield	Reaction Conditions	Operation in experiment
71.5%	With sulfuric acid/sulfolane at 200℃; for 0.0333333h;

Reference： [1]Kawamoto, Haruo; Saito, Shinya; Saka, Shiro [Carbohydrate Research, 2008, vol. 343, # 2, p. 249 - 255]

44
[ 50-99-7 ]
[ 67-47-0 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 58.2% 2: 12.8%	With 2H⁽¹⁺⁾O₄₀PW₁₂^(3-)C₄H₅N₂O₃S⁽¹⁺⁾; sodium chloride In tetrahydrofuran; water at 180℃; for 6h; Autoclave; Inert atmosphere;
	With silica gel at 350℃; for 0.00555556h;
	With hydrogenchloride; biphenyl In water; dimethyl sulfoxide at 120℃;	3.2. Representative procedure for glucose conversion in DMSO/Water Glucose reactions and subsequent NMR experiments were conductedin a closed lid NMR tube due to the volatility of HCl acidcatalyst. Solutions of glucose (56 mM) in various ratios of DMSO/Water mixtures with HCl (5.6 mM) and biphenyl (2 mM) wereprepared in advance. Each NMR tube evenly charged with 0.6 mLsolution was then placed into the pre-equilibrated oil-bath atpre-determined temperatures. Reactions were quenched by rapidlyinserting the tubes into ice water. Subsequent NMR 1H experimentswere performed. The 1H NMR peaks used for quantification:biphenyl d 7.66 (m, 1H, H3), 7.46 (m, 1H, H2), 7.36 (m, 1H, H1);glucose d 4.94 (d, 1H, J = 3.6 Hz, H1-a), 4.20 (d, 1H, J = 7.5 Hz,H1-b); for levoglucosan d 5.15 (s, 2H, H1-b), 4.76 (dd, 1H, H3);for HMF, d 9.54 (s, 1H, H1), 7.49 (d, 1H, J = 3.6 Hz, H2), 6.60 (d,1H, J = 3.6 Hz, H3), 4.50 (s, 2H, H6).

Reference： [1]Zhao, Pingping; Cui, Hongyou; Zhang, Yunyun; Zhang, Yuan; Wang, Yong; Zhang, Yali; Xie, Yujiao; Yi, Weiming [ChemistryOpen, 2018, vol. 7, # 10, p. 824 - 832]
[2]Location in patent: experimental part Locas, Carolina Perez; Yaylayan, Varoujan A. [Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 15, p. 6717 - 6723]
[3]Qian, Xianghong; Liu, Dajiang [Carbohydrate Research, 2014, vol. 388, # 1, p. 50 - 60]

45
[ 111-87-5 ]
[ 5391-18-4 ]
[ 50-99-7 ]
[ 29781-80-4 ]
[ 498-07-7 ]
butyl-D-glucofuranoside [ No CAS ]
[ 29836-26-8 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 1790 - 1795

46
[ 2280-44-6 ]
1,6-anhydro-β-D-glucofuranose [ No CAS ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 30%	With Amberlyst-15 In N,N-dimethyl-formamide at 119.84℃; for 3h; regioselective reaction;
1: 15% 2: 17%	With Amberlyst-15 In N,N-dimethyl-formamide at 99.84℃; for 3h; regioselective reaction;

Reference： [1]Location in patent: scheme or table Takagaki, Atsushi; Ebitani, Kohki [Chemistry Letters, 2009, vol. 38, # 7, p. 650 - 651]
[2]Location in patent: scheme or table Takagaki, Atsushi; Ebitani, Kohki [Chemistry Letters, 2009, vol. 38, # 7, p. 650 - 651]

47
[ 100-39-0 ]
[ 498-07-7 ]
[ 33208-48-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With barium(II) oxide In N,N-dimethyl-formamide at 60℃; Inert atmosphere; regioselective reaction;
84.1%	Stage #1: levoglucosan With barium(II) hydroxide Stage #2: benzyl bromide
80%	Stage #1: levoglucosan With barium(II) oxide In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 24 - 60℃; for 4h; Inert atmosphere;

59%

With barium(II) oxide In N,N-dimethyl-formamide at 91℃; for 0.366667h; Flow reactor;

4.3.1. 1,6-Anhydro-2,4-di-O-benzyl-β-D-glucopyranose (2) Levoglucosan 1 (200 mg, 1.2 mmol) was dissolved in anhydrousN,N-dimethylformamide (7 mL) and loaded into an 8-mL stainless steelsyringe. Benzyl bromide (0.75 mL, 6.3 mmol) was dissolved in N,N-dimethylformamide(6.25 mL) and loaded into a separate 8-mL stainlesssteel syringe. A reactor coil high purity PFA tubing (0.04 I.D., 381 cm(12.5 ft), 3 mL) was placed in a hot bath at 91 °C to warm the reactionsolution. The levoglucosan and benzyl bromide solutions were flowedtogether at a flowrate of 0.26 mL/min through the PFA tubing into thepacked barium oxide column (3.0 g, 2.7 mL void volume,25 cm×4.6mm I.D.) with a residence time of 22 min. The reactionsolution was collected at steady state in a flask containing methanol(0.5 mL) to quench the reaction. The reaction mixture was diluted withdichloromethane (10 mL) and washed with water (10 mL), brine(10 mL), and lithium chloride solution (10 mL). The organic layer wascollected, dried over anhydrous sodium sulfate and concentrated undervacuum via rotary evaporation. The residue was subjected to columnpurification via Teledyne ISCO CombiFlash Rf 200i in hexane/ethylacetate in a stepwise gradient with elution of compound in 15% ethylacetate to provide 2 as a white solid (0.25 g, 0.73 mmol, 59%). See Fig.S4 in supporting information. Rf 0.46 (1:1 hexane: ethyl acetate); 1HNMR (500 MHz, chloroform-d) δ=7.44-7.29 (m, 10 H, Ph), 5.47 (s,1 H, H-1), 4.77-4.67 (m, 5 H, CH2 Ph), 4.59 (d, J=4.9 Hz, 1 H, H-5),3.89 (t, J=4.1 Hz, 1 H, H-3), 3.83 (d, J=7.3 Hz, 1 H, H-6), 3.68 (dd,J=5.4, 7.3 Hz, 1 H, H-6), 3.36 (d, J=3.4 Hz, 1 H, H-2), 3.28 (d,J=3.9 Hz, 1 H, H-4), 2.20 (bs, 1 H, OH).

Reference： [1]Location in patent: scheme or table Zhu, Xiangming; Dere, Ravindra T.; Jiang, Junyan; Zhang, Lei; Wang, Xiaoxia [Journal of Organic Chemistry, 2011, vol. 76, # 24, p. 10187 - 10197]
[2]Bai, Chaolumen; Budragchaa, Davaanyam; Yoshida, Takashi [Carbohydrate Research, 2017, vol. 446-447, p. 52 - 60]
[3]St-Gelais, Jacob; Côté, Émilie; Lainé, Danny; Johnson, Paul A.; Giguère, Denis [Chemistry - A European Journal, 2020, vol. 26, # 59, p. 13499 - 13506]
[4]Marion, Keevan C.; Wooke, Zachary; Pohl, Nicola L.B. [Carbohydrate Research, 2018, vol. 468, p. 23 - 29]

48
[ 64-17-5 ]
[ 498-07-7 ]
[ 13984-57-1 ]
[ 3128-06-1 ]

Yield	Reaction Conditions	Operation in experiment
45.41%	With Amberlyst 70 In water at 170℃; for 3h; Autoclave; Inert atmosphere;

Reference： [1]Hu, Xun; Wu, Liping; Wang, Yi; Mourant, Daniel; Lievens, Caroline; Gunawan, Richard; Li, Chun-Zhu [Green Chemistry, 2012, vol. 14, # 11, p. 3087 - 3098]

49
[ 106-96-7 ]
[ 498-07-7 ]
[ 1000416-70-5 ]

Yield	Reaction Conditions	Operation in experiment
99.8%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at 0 - 20℃; for 39h; Inert atmosphere; Darkness;
75%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide Inert atmosphere;

Reference： [1]Lepage, Mathieu L.; Bodlenner, Anne; Compain, Philippe [European Journal of Organic Chemistry, 2013, # 10, p. 1963 - 1972]
[2]Fu, Liye; Li, Lingyao; Wang, Jun; Knickelbein, Kyle; Zhang, Lin; Milligan, Ian; Xu, Yi; O'Hara, Kylie; Bitterman, Lindsay; Du, Wenjun [Chemical Communications, 2014, vol. 50, # 84, p. 12742 - 12745]

50
[ 498-07-7 ]
Cellobiose [ No CAS ]
[ 50-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; zinc(II) chloride at 70℃; for 0.25h;	4 Example 4 - Anhydroglucose conversion to hydrolysate. Example 4 - Anhydroglucose conversion to hydrolysate. [00156] 1 ,6-Anhydroglucose (levoglucosan) was mixed with 12 times its weight of a 70%> ZnCl2 solution containing additional 0.4 molal of HCl and kept at 70°C. Samples of hydrolysate were diluted with water and the liquid analyzed with a HPLC. Within 15 minutes (the first sample) the invariant composition equal to the example 2 was obtained, as confirmed by samples taken later in the process. This example shows that the same equilibrium attained in Examples 2 and 3 is obtained having anhydroglucose as the reactant.

Reference： [1]Current Patent Assignee: GOVERNMENT OF BRAZIL; BIOECON B.V.; Petrobras (in: Government of Brazil) - WO2013/110814, 2013, A1 Location in patent: Paragraph 00156

51
[ 498-07-7 ]
[ 842133-18-0 ]

Reference： [1]Patent: US2014/128595,2014,A1
[2]Journal of Organic Chemistry,2015,vol. 80,p. 2295 - 2309

52
[ 58479-61-1 ]
[ 498-07-7 ]
[ 1432591-75-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1H-imidazole In tetrahydrofuran at 0℃;	1 Synthesis of 1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose (II″) To a suspension solution of 1,6-anhydro-β-D-glucopyranose (1.83 g, 11.3 mmol) and imidazole (3.07 g, 45.2 mmol) in THF (10 mL) at 0° C. was added dropwise a solution of TBDPSCl (11.6 mL, 45.2 mmol) in THF (10 mL). After the 1,6-anhydro-β-D-glucopyranose was consumed, water (10 mL) was added and the mixture was extracted twice with EtOAc (20 mL each), washed with brine (10 mL), dried (Na2SO4) and concentrated. Column chromatography (eluting with 1:20 EtOAc/n-heptane) afforded 2,4-di-O-tert-butyldiphenylsilyl-1,6-anhydro-β-D-glucopyranose (5.89 g, 81%). [0218] 1H NMR (400 MHz, CDCl3) δ 7.82-7.70 (m, 8H), 7.49-7.36 (m, 12H), 5.17 (s, 1H), 4.22 (d, J=4.8 Hz, 1H), 3.88-3.85 (m, 1H), 3.583-3.579 (m, 1H), 3.492-3.486 (m, 1H), 3.47-3.45 (m, 1H), 3.30 (dd, J=7.4, 5.4 Hz, 1H), 1.71 (d, J=6.0 Hz, 1H), 1.142 (s, 9H), 1.139 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 135.89 (CH×2), 135.87 (CH×2), 135.85 (CH×2), 135.83 (CH×2), 133.8 (C), 133.5 (C), 133.3 (C), 133.2 (C), 129.94 (CH), 129.92 (CH), 129.90 (CH), 129.88 (CH), 127.84 (CH2×2), 127.82 (CH2×2), 127.77 (CH2×4), 102.4 (CH), 76.9 (CH), 75.3 (CH), 73.9 (CH), 73.5 (CH), 65.4 (CH2), 27.0 (CH3×6), 19.3 (C×2).
81%	With 1H-imidazole In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Page/Page column 0216; 0217; 0218
[2]Henschke, Julian P.; Wu, Ping-Yu; Lin, Chen-Wei; Chen, Shi-Feng; Chiang, Pei-Chen; Hsiao, Chi-Nung [Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2295 - 2309]

53
[ 841-76-9 ]
[ 498-07-7 ]
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In 1,4-dioxane; dibutyl ether at 20 - 135℃; for 150h;	42 Example 42 Synthesis of 1-C-phenyl-β-D-glucopyranoside((2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol; (1S)-1-C-phenyl Glucoside; (Ia)) To a suspension of 1,6-anhydro-β-D-glucopyranose (162 mg, 1.0 mmol) in dioxane (5 mL) was added Ph3Al (6.0 mL, 6.0 mmol, 1.0 M in Bu2O) at ambient temperature. The mixture was then heated to 135° C. (external bath temperature) for 150 hours. The mixture was cooled to ambient temperature and diluted with THF (5 mL), and then water (0.5 mL), 15% aqueous NaOH (0.25 mL) and diatomaceous earth were added sequentially. The mixture was stirred for 1 hour and MgSO4 (1 g) was added and then was filtered. To the filtered solid was added MeOH (5 mL) and 15% aqueous NaOH (0.12 mL). The suspension was stirred for 1 hour and then filtered again. The filtrates were combined and concentrated. The residue was purified by column chromatography (eluting with 1:10 MeOH/DCM) affording 1-C-phenyl-β-D-glucopyranoside (170 mg, 71%).
51%	Stage #1: levoglucosan With diisobutylaluminium hydride In toluene at 20℃; for 0.116667h; Inert atmosphere; Schlenk technique; Stage #2: triphenylaluminium In dibutyl ether; toluene at 140℃; for 48h;

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0320; 0321
[2]Henschke, Julian P.; Lin, Chen-Wei; Wu, Ping-Yu; Tsao, Wen-Shing; Liao, Jyh-Hsiung; Chiang, Pei-Chen [Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 5189 - 5195]

54
[ 18162-48-6 ]
[ 498-07-7 ]
1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 36%	With 1H-imidazole In tetrahydrofuran at 0℃;	17 Synthesis of 1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranose (II′″″) and 1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose (II′) To a suspension solution of 1,6-anhydro-β-D-glucopyranose (5.0 g, 30.8 mmol) and imidazole (14.7 g, 216 mmol) in THF (40 mL) at 0° C. was added dropwise a solution of TBSCl (23.2 g, 154 mmol) in THF (10 mL), and the mixture was stirred at ambient temperature overnight. After 1,6-anhydro-β-D-glucopyranose had been consumed, water (50 mL) was added and the mixture was extracted twice with EtOAc (100 mL each) and concentrated. Column chromatography (eluting with 1:10 DCM/n-heptane) afforded 1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranose (6.4 g, 41%) as a white solid. 1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose (4.3 g, 36%) was isolated separately as a white powder. 1,6-anhydro-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranose (II′″″): [0259] 1H NMR (400 MHz, CDCl3) δ 5.28-5.27 (m, 1H), 4.37-4.35 (m, 1H), 4.10 (dd, J=6.8, 0.8 Hz, 1H), 3.67 (dd, J=6.4, 6.4 Hz, 1H), 3.62-3.60 (m, 1H), 3.50 (d, J=1.2 Hz, 1H), 3.45 (d, J=1.2 Hz, 1H), 0.94 (s, 9H), 0.93 (s, 9H), 0.92 (s, 9H), 0.12 (s, 3H), 0.113 (s, 6H), 0.105 (s, 3H), 0.100 (s, 3H), 0.096 (s, 3H). 1,6-anhydro-2,4-di-O-tert-butyldimethylsilyl-β-D-glucopyranose (II′) [0260] 1H NMR (400 MHz, CDCl3) δ 5.29 (s, 1H), 4.39 (d, J=4.8 Hz, 1H), 3.86 (d, J=7.2 Hz, 1H), 3.68 (dd, J=7.2, 5.2 Hz, 1H), 3.55-3.52 (m, 2H), 3.64-3.45 (m, 1H), 2.09 (d, J=5.2 Hz, 1H, OH), 0.943 (s, 9H), 0.938 (s, 9H), 0.140 (s, 3H), 0.130 (s, 6H), 0.126 (s, 3H).
36%	With 1H-imidazole In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Page/Page column 0257; 0258; 0259; 0260
[2]Henschke, Julian P.; Wu, Ping-Yu; Lin, Chen-Wei; Chen, Shi-Feng; Chiang, Pei-Chen; Hsiao, Chi-Nung [Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2295 - 2309]

55
[ 498-07-7 ]
[ 98-80-6 ]
[ 32741-93-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	In toluene for 15h; Reflux; Dean-Stark;	26 Example 26 Synthesis of 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate (XIa) A mixture of 1,6-anhydro-β-D-glucopyranose (5 g, 30.8 mmol) and phenylboronic acid (3.76 g, 30.8 mmol) in PhMe (150 mL) was heated under reflux in a Dean-Stark apparatus for 15 hours. The mixture was cooled to ambient temperature and the white precipitate was filtered and washed with PhMe (10 mL) to give the 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate (4.90 g, 64%). [0284] 1H NMR (400 MHz, CDCl3) δ 7.83-7.87 (m, 2H), 7.46-7.51 (m, 1H), 7.37-7.42 (m, 2H), 5.65 (t, J=2.4 Hz, 1H), 4.63-4.67 (m, 1H), 4.58 (d, J=8.0 Hz, 1H), 4.19-4.22 (m, 1H), 4.12-4.16 (m, 1H), 4.08-4.10 (m, 1H), 3.94 (dd, J=7.6 Hz, 4.8 Hz, 1H), 3.44 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 134.3, 131.2, 127.7, 101.7, 76.5, 70.3, 70.2, 69.0, 66.2.
	In toluene Inert atmosphere; Dean-Stark;

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0282; 0283; 0284
[2]Henschke, Julian P.; Lin, Chen-Wei; Wu, Ping-Yu; Tsao, Wen-Shing; Liao, Jyh-Hsiung; Chiang, Pei-Chen [Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 5189 - 5195]

56
[ 1765-93-1 ]
[ 498-07-7 ]
[ 1432591-87-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	In toluene for 15h; Reflux; Dean-Stark;	30 Example 30 Synthesis of 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-fluorophenyl)boronate (XIf) A solution of 1,6-anhydro-β-D-glucopyranose (2.5 g, 15.4 mmol) and 4-fluorophenylboronic acid (2.15 g, 15.4 mmol) in PhMe (70 mL) was heated to reflux under Dean-Stark apparatus for 15 hours. The reaction was cooled and the white precipitate was filtrated. The white precipitate was washed with PhMe (10 mL) to give 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-fluorophenyl)boronate (2.86 g, 70%). [0294] 1H NMR (400 MHz, CDCl3) δ 7.81-7.86 (m, 2H), 7.04-7.10 (m, 2H), 5.64 (t, J=2.4 Hz, 1H), 4.62-4.64 (m, 1H), 4.58 (d, J=8.0 Hz, 1H), 4.18-4.22 (m, 1H), 4.10-4.15 (m, 1H), 4.07-4.09 (m, 1H), 3.94 (dd, J=8.0 Hz, 4.8 Hz, 1H), 3.42 (d, J=8.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 165.1 (d, J=248 Hz), 136.5 (d, J=8.2 Hz), 114.7 (d, J=20.0 Hz), 101.6, 76.5, 70.3, 70.1, 69.0, 66.2.

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0292;0293; 0294

57
[ 5720-07-0 ]
[ 498-07-7 ]
[ 1432591-88-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene for 15h; Reflux; Dean-Stark;	32 Example 32 Synthesis of 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-methoxylphenyl)boronate (XId) A solution of 1,6-anhydro-β-D-glucopyranose (2.5 g, 15.4 mmol) and 4-methoxylphenylboronic acid (2.35 g, 15.4 mmol) in PhMe (70 mL) was heated under reflux in a Dean-Stark apparatus for 15 hours. The reaction was cooled to ambient temperature give a white precipitate, which was filtered and washed with PhMe (10 mL) yielding 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-methoxylphenyl)boronate (4.28 g, 99%). [0299] 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 2H), 6.92 (d, J=8.8 Hz, 2H), 5.63 (t, J=2.4 Hz, 1H), 4.62-4.64 (m, 1H), 4.57 (d, J=7.6 Hz, 1H), 4.17-4.19 (m, 1H), 4.10-4.14 (m, 1H), 4.05-4.08 (m, 1H), 3.93 (dd, J=7.6 Hz, 4.8 Hz, 1H), 3.85 (s, 3H), 3.45 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 162.1, 136.0, 113.3, 101.7, 76.6, 70.3, 70.2, 68.9, 66.2, 55.1.

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0297;0298; 0299

58
[ 1582-24-7 ]
[ 498-07-7 ]
[ 1432591-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 2h; Reflux; Dean-Stark;	35 Example 32 Synthesis of 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-methoxylphenyl)boronate (XId) A solution of 1,6-anhydro-β-D-glucopyranose (2.5 g, 15.4 mmol) and 4-methoxylphenylboronic acid (2.35 g, 15.4 mmol) in PhMe (70 mL) was heated under reflux in a Dean-Stark apparatus for 15 hours. The reaction was cooled to ambient temperature give a white precipitate, which was filtered and washed with PhMe (10 mL) yielding 1,6-anhydro-β-D-glucopyranose 2,4-O-(4′-methoxylphenyl)boronate (4.28 g, 99%). [0299] 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 2H), 6.92 (d, J=8.8 Hz, 2H), 5.63 (t, J=2.4 Hz, 1H), 4.62-4.64 (m, 1H), 4.57 (d, J=7.6 Hz, 1H), 4.17-4.19 (m, 1H), 4.10-4.14 (m, 1H), 4.05-4.08 (m, 1H), 3.93 (dd, J=7.6 Hz, 4.8 Hz, 1H), 3.85 (s, 3H), 3.45 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 162.1, 136.0, 113.3, 101.7, 76.6, 70.3, 70.2, 68.9, 66.2, 55.1.

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0304; 0305; 0306

59
[ 5980-97-2 ]
[ 498-07-7 ]
[ 1432591-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 12h; Reflux; Dean-Stark;	37 Example 37 Synthesis of 1,6-anhydro-β-D-glucopyranose 2,4-O-(2′,4′,6′-trimethylphenyl)boronate (XIb) A solution of 1,6-anhydro-β-D-glucopyranose (162 mg, 1.0 mmol) and 2,4,6-trimethylphenyl)boronic acid (164 mg, 1.0 mmol) in PhOMe (5 mL) was heated under reflux in Dean-Stark apparatus for 12 hours to give crude 1,6-anhydro-β-D-glucopyranose 2,4-O-(2′,4′,6′-trimethylphenyl)boronate, which was directly used in the next step without further purification.

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0309; 0310

60
[ 818-08-6 ]
[ 498-07-7 ]
[ 116391-03-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene for 12h; Reflux; Dean-Stark;	40 Example 40 Synthesis of 2,4-O-dibutylstannylene-1,6-anhydro-β-D-glucopyranose (XIIa) A solution of 1,6-anhydro-β-D-glucopyranose (1.0 g, 6.2 mmol) and dibutyltin oxide (1.5 g, 6.2 mmol) in PhMe (40 mL) was heated under reflux for 15 hours with continual removal of water from the reaction system in Dean-Stark apparatus. The product mixture was evaporated under reduced pressure until the solvent (PhMe) has been removed. The residue was cooled to ambient temperature affording 2,4-O-dibutylstannylene-1,6-anhydro-β-D-glucopyranose (2.42 g, 99%). [0317] 1H NMR (400 MHz, CDCl3) δ 5.47 (t, J=2.0 Hz, 1H), 4.49-4.53 (m, 1H), 4.27 (d, J=7.6 Hz, 1H), 3.76-3.80 (m, 2H), 3.69-3.73 (m, 1H), 3.65-3.68 (m, 1H), 3.78 (d, J=7.2 Hz, 1H), 1.66-1.75 (m, 4H), 1.27-1.45 (m, 8H), 0.92-0.97 (m, 6H).

Reference： [1]Current Patent Assignee: SCINOPHARM TAIWAN, LTD. - US2014/128595, 2014, A1 Location in patent: Paragraph 0315; 0316; 0317

61
[ 9004-34-6 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 500℃; Pyrolysis;
	With nano zeolite supported on clay at 500℃; Pyrolysis;	2.2. micro-pyrolyzer-GC/FID experiments General procedure: The pyrolysis and catalytic pyrolysis experiments were conducted using a single-shot micro-pyrolyzer equipped with an auto sampler (Frontier Laboratories, Japan). The micro-pyrolyzer was directly connected to a GC analyzer with a FID, which was automatically conducted by the operation control in a combination system between the micro-reactor and gas analyzer. For the experimental conditions, the furnace was mainatined at a temperature of 500° C. The reactant of about 500 g was first placed into a stainless steel sample cup and then the catalyst of about 5 g was loaded at upper of reactant. Finally, the quartz wool was put at top of the sample cup and thus both the catalyst and reactant were fixed within sample cup, which was dropped into the furnace of pyrolyzer with very short drop time (with unitof milliseconds) under the flow of 20 cm/s helium gas. In product analysis, the products were separated using an alloy capillary column (Ultra Alloy-1701, Frontier Laboratories, Japan) with a carrier gas flow of 1 ml/min. For GC conditions, the injector temperature and split ratio were 300 °C and 1:100, respectively, and the oven temperature program began at 35 °C, held 3 min at 35 °C and then heated to 300 °C at 5 C/min, held for 4 min at that temperature.
	Pyrolysis;

Reference： [1]Park, Young-Kwon; Jun, Bo Ram; Park, Sung Hoon; Jeon, Jong-Ki; Lee, See Hoon; Kim, Seong-Soo; Jeong, Kwang-Eun [Journal of Nanoscience and Nanotechnology, 2014, vol. 14, # 7, p. 5120 - 5123]
[2]Lee, Kyong-Hwan [Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 5, p. 4631 - 4637]
[3]Bacik, John-Paul; Klesmith, Justin R.; Whitehead, Timothy A.; Jarboe, Laura R.; Unkefer, Clifford J.; Mark, Brian L.; Michalczyk, Ryszard [Journal of Biological Chemistry, 2015, vol. 290, # 44, p. 26638 - 26648]

62
1-methyl-3-(2,2,2-trichloroethoxysulfuryl)-3H-imidazol-1-ium triflate [ No CAS ]
[ 498-07-7 ]
1,6-anhydro-2-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,4-bis-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-4-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 17% 2: 14% 3: 30%	With 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose In tetrahydrofuran at 20℃; Inert atmosphere;	, entry 1) 1-Methylimidazole (225 μL, 2.82 mmol) and SMIS (1.25 g, 2.82 mmol) were added to a solution of 11 (305.6 mg, 1.885 mmol) in THF (5 mL) while stirring at rt overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, and then treated as usual. The residue was purified on a column of silica gel (5:1-1:1 toluene-EtOAc) to give 12 (123.7 mg), 13 (97.7 mg), and 14 (331.4 mg) as crystals in 17%, 14%, and 30% yields, respectively.

Reference： [1]Matsushita, Kenya; Sato, Yuta; Funamoto, Shinji; Tamura, Jun-Ichi [Carbohydrate Research, 2014, vol. 396, p. 14 - 24]

63
[ 1185733-70-3 ]
[ 498-07-7 ]
1,6-anhydro-2-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,3,4-tris-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,4-bis-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-4-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 17% 2: 23% 3: 15% 4: 7%	With 1,2-dimethyl-1H-imidazole In tetrahydrofuran at 20℃; Inert atmosphere;	, entry 3) A 1.0 M solution of 1,2-dimethylimidazole in THF (1.4 mL, 1.4 mmol) and SDIS (630.9 mg, 1.379 mmol) was added to a solution of 11 (110.4 mg, 680.9 μmol) in THF (3.8 mL) while stirring at rt overnight. The reaction mixture was diluted with CHCl3, and then treated as usual. The residue was subjected to a column of gel permeation (LH-20, 1:1 CHCl3-MeOH) to give a mixture of 12-15. The mixture was purified on a column of silica gel (toluene to 1:6 toluene-EtOAc) to give 12 (43.4 mg), 13 (58.4 mg), 14 (58.5 mg), and 15 (39.1 mg) in 17%, 23%, 15%, and 7% yields, respectively.

Reference： [1]Matsushita, Kenya; Sato, Yuta; Funamoto, Shinji; Tamura, Jun-Ichi [Carbohydrate Research, 2014, vol. 396, p. 14 - 24]

64
[ 1185733-70-3 ]
[ 498-07-7 ]
1,6-anhydro-2,3,4-tris-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6-anhydro-2,4-bis-O-(2,2,2-trichloroethoxysulfo)-β-D-glucopyranose [ No CAS ]
1,6:3,4-dianhydro-2-O-(2,2,2-trichloroethoxysulfo)-β-D-galactopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 16% 3: 7%	With 1,2-dimethyl-1H-imidazole In dichloromethane at 20℃; Inert atmosphere;	, entry 2) A 1.0 M solution of 1,2-dimethylimidazole in CH2Cl2 (1.1 mL, 1.1 mmol) and SDIS (489 mg, 1.07 mmol) was added to a solution of 11 (86.1 mg, 531 μmol) in CH2Cl2 (3 mL) while stirring at rt overnight. The reaction mixture was diluted with CHCl3, and treated as usual. The residue was purified on a column of gel permeation (LH-20, 1:1 CHCl3-MeOH) to give 15 (105.5 mg) in 25% yield in addition to a mixture of 14 and 16, which was separated on a column of silica gel (toluene to 20:1-4:1 toluene-EtOAc) to give 14 (48.7 mg) and 16 (12.7 mg) as crystals in 16% and 7% yields, respectively.

Reference： [1]Matsushita, Kenya; Sato, Yuta; Funamoto, Shinji; Tamura, Jun-Ichi [Carbohydrate Research, 2014, vol. 396, p. 14 - 24]

65
[ 106-95-6 ]
[ 498-07-7 ]
1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20 - 0℃; for 1h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at -20 - 20℃;	1,6-Anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose (5b). To a solution of levoglucosan (1 equiv., 1 g,6.11 mmol) in DMF (45 mL) at -20 °C was added sodium hydride (60% in oil, 4 equiv., 0.98 g,24.4 mmol) portionwise. The cooling bath was allowed to reach 0°C within 1 h, then it was cooledagain to -20 °C and allyl bromide (4.5 equiv., 2.4 mL, 27.6 mmol) was added under vigorous stirring.The reaction mixture was stirred overnight at r.t. The mixture was diluted with water and extractedwith diethyl ether (3 x 100 mL). The organic phases are combined and washed 5 times with water,dried with Na2SO4, filtered, and concentrated to afford a yellow oil which was purified by flashchromatography (Petroleum Ether/EtOAc, 9/1 to 1/1), to give 5b (1.63 g, 5.77 mmol) as a yellow oil in95% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) 5.92-5.79 (m, 3H, OCH2CHCH2), 5.37 (s, 1H, H-1),5.26-5.12 (m, 6H, OCH2CHCH2), 4.51 (m, 1H, H-5), 4.08-4.02 (m, 6H, OCH2CHCH2), 3.85 (dd, J = 7.1,0.8 Hz, 1H, H-6), 3.64 (dd, J = 6.8, 6.0 Hz, 1H, H-6), 3.45 (m, 1H, H-3), 3.24 (m, 1H, H-4), 3.21 (m, 1H,H-2). The analyses are in good agreement with the experimental data reported in literature [21].
90%	Stage #1: levoglucosan With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20 - 0℃; for 1h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at -20 - 20℃; Inert atmosphere;	2,3,4-Tri-O-allyl-1,6-anhydro-β-d-glucopyranose Sodium hydride (60% in oil, 500mg, 12.5mmol) was added to a solution of 1,6-anhydro-β-d-glucopyranose (530mg, 3.27mmol) in anhydrous N,N-dimethylformamide (15mL) under cooling (-20°C) and stirring. The cooling bath temperature was allowed to reach 0°C within 1h, then it was cooled again to-20°C and allyl bromide (1.3mL, 15mmol) was added under vigorous stirring. The reaction mixture was stirred overnight at room temperature. It was then diluted with water, extracted with diethyl ether, the organic extract was dried (Na2SO4) and concentrated to afford crude product (1.12g). Chromatography in ethyl acetate-light petroleum 1:5 yielded syrupy 2,3,4-tri-O-allyl-1,6-anhydro-β-d-glucopyranose (835mg, 90%). The product was unstable and slowly polymerized at room temperature. It could be stored at-30°C for a few weeks, the purity being >95% according to NMR. 1H NMR [300MHz, CDCl3]: δ (ppm) 3.25 (dd, 3J(H1,2)=1.3Hz and 3J(H2,3)=1.3Hz, 1H, H2), 3.28 (dd, 3J(H4,5)=1.3Hz and 3J(H3,4)=3.9Hz, 1H, H4), 3.49 (dddd, 4J(H1,3)=1.3Hz, 4J(H3,5)=1.3Hz, 3J(H2,3)=1.3Hz and 3J(H3,4)=3.9Hz, 1H, H3), 3.68 (dd, 2J(H6,6′)=7.1Hz and 3J(H6′,5)=5.8Hz, 1H, H6′), 3.89 (dd, 2J(H6,6′)=7.1Hz and 3J(H6,5)=1.1Hz, 1H, H6), 4.09 (m, 3× 2H, OCH2CH), 4.55 (dddd, 4J(H3,5)=1.3Hz, 3J(H4,5)=1.3Hz, 3J(H6,5)=1.1Hz and 3J(H6′,5)=5.8Hz, 1H, H5), 5.31 (m, 3× 2H, OCH2CHCH2), 5.41 (dd, 3J(H1,2)=1.3Hz and 4J(H1,3)=1.3Hz, 1H, H1), 5.90 (m, 3× 1H, OCH2CHCH2). 13C {1H} NMR [300MHz, CDCl3]: δ (ppm) 65.43 (C6), 70.40, 70.97 and 71.19 (OCH2CHCH2), 74.30 (C5), 76.62 (C2 or C3), 76.65 (C2 or C3), 77.28 (C4), 100.75 (C1), 117.37, 117.66 and 117.80 (OCH2CHCH2), 134.79, 134.83 and 134.94(OCH2CHCH2).

Reference： [1]Céspedes Dávila, Maria F.; Schneider, Jérémy P.; Godard, Amélie; Hazelard, Damien; Compain, Philippe [Molecules, 2018, vol. 23, # 4]
[2]Strašák, Tomáš; Karban, Jindřich; Št'Astná, Lucie Červenková; Maixnerová, Lucie; Březinová, Anna; Bernard, Martin; Fajgar, Radek [Journal of Organometallic Chemistry, 2014, vol. 768, p. 115 - 120]

66
<SUP>13</SUP>C-C₁-glucopyranose [ No CAS ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
10%	With sulfuric acid In water at 130℃; for 0.0166667h; Green chemistry;

Reference： [1]Qi, Long; Mui, Yiu Fung; Lo, See Wing; Lui, Matthew Y.; Akien, Geoffrey R.; Horvath, Istvan T. [ACS Catalysis, 2014, vol. 4, # 5, p. 1470 - 1477]

67
bis(3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl)chloroalane [ No CAS ]
[ 498-07-7 ]
[ 842133-18-0 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 5189 - 5195

68
[ 498-07-7 ]
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: levoglucosan With diisobutylaluminium hydride In toluene at 20℃; for 0.116667h; Inert atmosphere; Schlenk technique; Stage #2: Ph_2.5AlCl_0.5 In tetrahydrofuran; dibutyl ether; toluene at 140℃; for 24h;

Reference： [1]Henschke, Julian P.; Lin, Chen-Wei; Wu, Ping-Yu; Tsao, Wen-Shing; Liao, Jyh-Hsiung; Chiang, Pei-Chen [Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 5189 - 5195]

69
[ 498-07-7 ]
[ 492-62-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfuric acid In water at 110℃; for 24h;

Reference： [1]Santhanaraj, Daniel; Rover, Marjorie R.; Resasco, Daniel E.; Brown, Robert C.; Crossley, Steven [ChemSusChem, 2014, vol. 7, # 11, p. 3132 - 3137]

70
[ 146137-72-6 ]
[ 498-07-7 ]
2-(2-fluoro-6-iodobenzoyl)-1,6-anhydro-β-D-glucose [ No CAS ]
C₁₃H₁₂FIO₆ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 7403 - 7407

71
[ 498-07-7 ]
[ 37112-31-5 ]

Yield	Reaction Conditions	Operation in experiment
53.6%	With sulfuric acid In sulfolane at 215℃; Inert atmosphere;	11 EXAMPLES 1 -14 In each of Examples 1 -14 the conversion of carbohydrate-containing feedstock to levoglucosenone was conducted in a 50 mL glass stirred tank reactor according to the following procedure. At the beginning of a run the reactor was initially filled with 25 mL of sulfolane containing sulfuric acid at a concentration as shown in Table I. The reactor outlet was opened and the pressure was reduced to 20 kPa using a vacuum pump. The reactor was then heated to the reaction temperature shown in Table I using a molten metal bath. Upon reaching reaction temperature, a preheated solution of sulfuric acid in sulfolane was pumped into the reactor through a sub-surface dip leg. The flowrate of the solution of sulfuric acid in sulfolane was set to obtain the desired residence time shown in Table I. At the same time, preheated nitrogen purge gas was fed to the reactor at a flow rate of 200 mL min"1 through another subsurface dip leg. The liquid level in the reactor was maintained at 25 mL during the reaction by use of a dip tube at the reactor outlet. During the run, liquid effluent from the reactor flowed through a two way valve to one of two 1000 mL sample collection flasks. The valve allowed one flask to be filled while the other was isolated from the system and emptied. The outlets of the sample collection flasks were connected to a vacuum pump to maintain the desired system pressure. After stable reactor temperature, flow rates, and reactor pressure were achieved (circa 5 min), the solid carbohydrate-containing feed was introduced to the reactor by an auger type solid feeder located at the top of the reactor. After an amount of time equal to 5 times the residence time, the two way valve was switched and liquid effluent was diverted to an empty product collection flask to collect a steady-state sample of the reaction mixture from the reactor. After collecting a sufficient amount of sample for analysis, the valve was switched again, and the steady state sample flask was removed from the system. The amount of levoglucosenone in the liquid sample was analyzed by GC-FID. The steady state molar yield of levoglucosenone was then calculated and is reported in Table I. COMPARATIVE EXAMPLE A Comparative Example A was performed following the procedure of Examples 1 -14 with reaction conditions as indicated in Table 1 , except that the carbohydrate-containing feed was pre-treated with acid before use and there was no continuous addition of acid solution to the reactor. The cellulose was impregnated with acid according to the following method. Equal parts by weight of aqueous 0.1 wt% sulfuric acid and cellulose were mixed to form a slurry. The water was then removed from the slurry by holding the sample in a 50° C vacuum oven overnight. The dried, acid-impregnated cellulose obtained in this manner contained 0.1 wt% acid based on total weight of the cellulose and acid. The acid concentration in sulfolane in the reactor calculated from the flow rate of acid and sulfolane to the reactor was 0.007 wt%. Table 1 . Reaction Conditions and Levoglucosenone Yield for Examples 1 -14 and Comparative Example A The results in Table I demonstrate production of levoglucosenone from cellulose, levoglucosan, glucose, and switchgrass as carbohydrate sources using the processes disclosed herein. Higher yields of levoglucosenone were obtained at higher temperature, as seen by the comparison of Examples 6 and 12, which used cellulose as feed, and also the series of Examples 7, 8, 9, 10, and 1 1 which used levoglucosan as feed. Examples 1 1 , 12, 13, and 14 demonstrated the best levoglucosenone yields, above 40 mole%, under reaction conditions which included higher temperature (215 °C) and lower residence time (3.3 - 3.8 minutes). The results for Example 4 and Example 5 demonstrated levoglucosenone yields comparable to that of Comparative Example A, which was performed under similar reaction conditions but using cellulose which had been pre-treated with acid and at an acid concentration in the reactor equivalent to 0.007 weight percent sulfuric acid in sulfolane.
	With propanesulfonic acid In tetrahydrofuran at 209.84℃; Inert atmosphere; Autoclave;

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2016/39996, 2016, A1 Location in patent: Page/Page column 17-20
[2]Oyola-Rivera, Oscar; He, Jiayue; Huber, George W.; Dumesic, James A.; Cardona-Martínez, Nelson [Green Chemistry, 2019, vol. 21, # 18, p. 4988 - 4999]

72
[ 9004-34-6 ]
[ 141-46-8 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 500℃; Pyrolysis;	2.2. micro-pyrolyzer-GC/FID experiments General procedure: The pyrolysis and catalytic pyrolysis experiments were conducted using a single-shot micro-pyrolyzer equipped with an auto sampler (Frontier Laboratories, Japan). The micro-pyrolyzer was directly connected to a GC analyzer with a FID, which was automatically conducted by the operation control in a combination system between the micro-reactor and gas analyzer. For the experimental conditions, the furnace was mainatined at a temperature of 500° C. The reactant of about 500 g was first placed into a stainless steel sample cup and then the catalyst of about 5 g was loaded at upper of reactant. Finally, the quartz wool was put at top of the sample cup and thus both the catalyst and reactant were fixed within sample cup, which was dropped into the furnace of pyrolyzer with very short drop time (with unitof milliseconds) under the flow of 20 cm/s helium gas. In product analysis, the products were separated using an alloy capillary column (Ultra Alloy-1701, Frontier Laboratories, Japan) with a carrier gas flow of 1 ml/min. For GC conditions, the injector temperature and split ratio were 300 °C and 1:100, respectively, and the oven temperature program began at 35 °C, held 3 min at 35 °C and then heated to 300 °C at 5 C/min, held for 4 min at that temperature.

Reference： [1]Lee, Kyong-Hwan [Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 5, p. 4631 - 4637]

73
[ 498-07-7 ]
[ 17371-37-8 ]

Yield	Reaction Conditions	Operation in experiment
58 %Spectr.	With p-benzoquinone In [D₃]acetonitrile at 50℃; for 2.5h; chemoselective reaction;

Reference： [1]Chung, Kevin; Waymouth, Robert M. [ACS Catalysis, 2016, vol. 6, # 7, p. 4653 - 4659]

74
[ 498-07-7 ]
[ 57-55-6 ]
[ 50-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 5 wt% ruthenium/carbon; water; hydrogen at 150℃; for 5h; Autoclave;

Reference： [1]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]

75
[ 498-07-7 ]
[ 2280-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	With water at 180℃; for 5h; Inert atmosphere; Autoclave;

Reference： [1]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]

76
[ 498-07-7 ]
[ 50-70-4 ]

Yield	Reaction Conditions	Operation in experiment
96.2%	With water; hydrogen at 180℃; for 5h; Autoclave;
	Multi-step reaction with 2 steps 1: hydrogen; water / 37503.8 Torr / Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave
	Multi-step reaction with 2 steps 1: hydrogen; water / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave

	Multi-step reaction with 2 steps 1: hydrogen; water / 5 h / 150 °C / 37503.8 Torr / Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave
	Multi-step reaction with 2 steps 1: hydrogen; water / 5 h / 150 °C / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave
	Multi-step reaction with 2 steps 1: water / 5 h / 180 °C / Inert atmosphere; Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave
	Multi-step reaction with 2 steps 1: water / 5 h / 180 °C / Inert atmosphere; Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave

Reference： [1]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[2]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[3]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[4]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[5]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[6]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[7]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]

77
[ 498-07-7 ]
[ 69-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogen; water / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 2 steps 1: hydrogen; water / 5 h / 180 °C / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 2 steps 1: hydrogen; water; 5 wt% ruthenium/carbon / 5 h / 150 °C / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave

	Multi-step reaction with 2 steps 1: hydrogen; water; 5 wt% ruthenium/carbon / 5 h / 180 °C / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: hydrogen; water / 37503.8 Torr / Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: hydrogen; water / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: hydrogen; water / 5 h / 150 °C / 37503.8 Torr / Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: hydrogen; water / 5 h / 150 °C / 37503.8 Torr / Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: water / 5 h / 180 °C / Inert atmosphere; Autoclave 2: hydrogen / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave
	Multi-step reaction with 3 steps 1: water / 5 h / 180 °C / Inert atmosphere; Autoclave 2: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 52505.3 Torr / Autoclave 3: hydrogen; 5 wt% ruthenium/carbon / water / 5 h / 180 °C / 37503.8 Torr / Autoclave

Reference： [1]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[2]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[3]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[4]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[5]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[6]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[7]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[8]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[9]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]
[10]Yin, Wang; Tang, Zhenchen; Venderbosch, Robertus Hendrikus; Zhang, Zheng; Cannilla, Catia; Bonura, Giuseppe; Frusteri, Francesco; Heeres, Hero Jan [ACS Catalysis, 2016, vol. 6, # 7, p. 4411 - 4422]

78
[ 9004-34-6 ]
[ 67-47-0 ]
[ 37112-31-5 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 10.4% 2: 10% 3: 20.5%	With phosphoric acid In tetrahydrofuran at 210℃; for 160h; Autoclave; Inert atmosphere;
1: 5.3% 2: 19.6% 3: 15.8%	With hydrogenchloride In tetrahydrofuran; water at 210℃; for 170h; Autoclave; Inert atmosphere;

Reference： [1]He, Jiayue; Liu, Mingjie; Huang, Kefeng; Walker, Theodore W.; Maravelias, Christos T.; Dumesic, James A.; Huber, George W. [Green Chemistry, 2017, vol. 19, # 15, p. 3642 - 3653]
[2]He, Jiayue; Liu, Mingjie; Huang, Kefeng; Walker, Theodore W.; Maravelias, Christos T.; Dumesic, James A.; Huber, George W. [Green Chemistry, 2017, vol. 19, # 15, p. 3642 - 3653]

79
[ 498-07-7 ]
[ 67-47-0 ]
[ 37112-31-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 31.5% 2: 5.5%	With sulfuric acid In tetrahydrofuran at 170℃; for 90h; Autoclave; Inert atmosphere;

Reference： [1]He, Jiayue; Liu, Mingjie; Huang, Kefeng; Walker, Theodore W.; Maravelias, Christos T.; Dumesic, James A.; Huber, George W. [Green Chemistry, 2017, vol. 19, # 15, p. 3642 - 3653]

80
C₆H₁₁O₈S₂^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide In water-d2
80 %Spectr.	With potassium hydroxide In water-d2 at 20℃; for 13h;

Reference： [1]Fairbanks, Antony J. [Carbohydrate Research, 2021, vol. 499]
[2]Meguro, Yasuhiro; Noguchi, Masato; Li, Gefei; Shoda, Shin-Ichiro [Organic Letters, 2018, vol. 20, # 1, p. 76 - 79]

81
[ 66963-60-8 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
170 g	With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 50℃; for 4h;	1 Preparation of Phenyl-6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-L-idopyranoside Modified and Optimized Procedure l,6-anhydro-3-O-benzyl- -L-idopyranose (150g, 0.6 mol) was dissolved in the mixture EtOAc/MeOH (1 : 1, 1200 ml) and hydrogenated over 10% Pd/C (15 g) at 50 °C, 5 atm for 4h. The mixture was cooled to 20 °C, filtered through Celite and evaporated under reduced pressure. The oily residue and DMAP (22 g, 0.18 mol) were dissolved in CH2C12 (400 ml) and Pyridine (404 ml, 5.0 mol) and the resulted mixture was cooled to 0 °C. Benzoyl chloride (276 g, 229 ml, 1.96 mol) was slowly added and the reaction was stirred for 3h at 20 °C (TLC monitoring). The volatiles were evaporated under reduced pressure and the solid residue was portioned between EtOAc (2L) and water (2L). The phases were separated, the organic one was washed with cold 2N aqueous HC1 (700 ml), water (500ml) and 10% aqueous NaHC03 (500 ml), dried over Na2S04, filtered and concentrated under reduced pressure to give ~300g of solid residue. The residue was crystallized from Isopropanol afforded 265g (94%) yield) of the desired tribenzoate as white solid.

Reference： [1]Current Patent Assignee: OPKO HEALTH INC - WO2018/35050, 2018, A1 Location in patent: Paragraph 0073

82
[ 498-07-7 ]
[ 107-21-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1% Ru/SiO2; silver(I) tungstate; hydrogen In water at 195℃; for 2.25h; Autoclave; Sealed tube;	4 Experimental Procedure for Examples 1 - 5 (1% - 2% l,6-anhydro- -D-glucose solutions): The reactions were run in 75 ml Hastelloy C batch autoclaves, with magnetic stir bars, to screen various conditions for the 1% - 2% l,6-anhydro- -D-glucose solutions in water. In typical experiments, 30ml of the 1% - 2% l,6-anhydro- -D-glucose solution was loaded into the autoclave. If less than 30ml of the feed was available, deionized water was added to make a total liquid volume of 30ml. Depending on the experiment, known amounts of hydrogenation catalyst and/or retro- Aldol catalysts were also added to the autoclave. The loaded autoclave was then purged three times with nitrogen, followed by hydrogen purge. The pressure was then raised to 2000 psig of hydrogen and the autoclave was sealed and left stirring to perform a leak test. [0043] After performing the leak test, the autoclave was de -pressurized to the target hydrogen pressure at room temperature, and closed. For a one step reaction, the temperature was ramped to 195 °C and held for varying durations including from 75 minutes to 225 minutes. After the last hold, the reactor was cooled to room temperature. A sample of the reactor contents was then taken, filtered and analyzed by High Pressure Liquid (0055) Chromatography (HPLC).

Reference： [1]Current Patent Assignee: SHELL PLC - WO2018/39109, 2018, A1 Location in patent: Paragraph 0041-0044

83
[ 14464-29-0 ]
[ 498-07-7 ]
[ 93173-18-3 ]

Yield	Reaction Conditions	Operation in experiment
34.4 g	With pyridine; Novozym 435; for 48h;	The compound shown in Formula 6 is dissolved in 1500 ml of pyridine and added to Novozym 435(immobilized Candida antarctica lipase) 20g,Acetic acid succinimide ester 47.2g, placed in a shaker controlled 30±1°C reaction for 48h,After filtration, the filtrate was concentrated to dryness under reduced pressure, dissolved in 500 ml of methylene chloride, washed with 500 ml of 1N diluted hydrochloric acid, and washed with 500 ml of water. The organic phases were combined, the organic phase was concentrated to dryness, 200 ml of toluene was added, and the mixture was stirred for 2 h. The solid precipitated and was filtered. drying,Formula 5The compound shown 34.4 g;

Reference： [1]Patent: CN107686495,2018,A .Location in patent: Paragraph 0036; 0069; 0070

84
[ 104-15-4 ]
[ 498-07-7 ]
[ 20204-80-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With pyridine at -10℃;	32.1 Step 1) [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl] - 4-methylbenzenesulfonic acid To a solution of (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3 .2.1 ]octane-2,3 ,4-triol (3.00 g, 18.5 mmol) in pyridine (18 mL) was added p-toluensulfonyl chloride (7.84 g, 40.7 mmol) at -10°C under N2. The mixture was stirred at -10 °C overnight. The mixture was quenched with water (300 mL) and stirred for 20 mm, and concentrated to remove water. The residue was dissloved in EtOAc (150 mL). The mixture was washed with saturated ammonium chloride solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 2/1) to give the title compound as an off-white solid (7.31 g, 84.0%).MS (ESI, pos. ion) m/z: 471.2[M+Hfb;1HNIVIR(400 IVIHz, DMSO) 7.79 (dd, J= 8.2, 4.8 Hz, 4H), 7.49 (dd, J 8.2, 3.0 Hz, 5H), 6.05 (d, J = 4.2 Hz, 1H), 5.27 (s, 1H), 4.54 (d, J = 5.3 Hz, 1H), 4.32 (s, 1H), 4.04 (s, 1H), 4.02 (d, J = 4.9 Hz, 1H), 3.59-3.52 (m, 2H), 2.46 (d, J = 4.7 Hz, 1H), 2.43 (s, 6H).

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2018/133858, 2018, A1 Location in patent: Paragraph 00318

85
[ 108-32-7 ]
[ 498-07-7 ]
poly(1,6-anhydro-β-D-glucopyranose-co-propylene carbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With 2-butynyltetramethylene sulfonium hexafluoroantimonate at 100℃; for 0.5h;	1 Under nitrogen atmosphere, into a sufficiently dried Schlenk tube, 13.0 g of 1, 6-anhydro-ß-D-glucopyranose (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 12.5 ml of dry propylene carbonate (manufactured by Sigma-Aldrich Co. ) and 66 mass % of 2-butynyltetramethylene sulfonium hexafluoroantimonate (65.8 Ll) (manufactured by ASAHI DENKA CO. , LTD. ) were charged. Then, the Schlenk tube was placed in an oil bath, and the oil bath was heated to 100 °C so as to thoroughly dissolve 1, 6-anhydro-ß-glucopyranose. Subsequently, the oil bath was furtherheatedto 130 °Cwhile stirring, so as to allowpolymerization to begin. After 30 minutes'reaction, the polymerization solution was added into methanol to stop the polymerization reaction. After removing the solvent, reprecipitation was repeated with water and methanol. The resultant solution was further dialyzed for purification and freeze-dried to obtain 5.3 g of multi-branched polysaccharide A in white powder. The yield was 41 %. The multi-branchedpolysaccharideAwassubjectedto1H-NHRandl 3 C-NMR analyses to confirm the structure. Moreover, the weight average molecular weight of the multi-branched polysaccharide Awas 20, 000 (light scattering method), and the branching degree was 0.38.

Reference： [1]Current Patent Assignee: SHOWA DENKO K K - WO2005/94777, 2005, A1 Location in patent: Page/Page column 31

86
[ 622-95-7 ]
[ 498-07-7 ]
(1R,2S,3S,4R,5R)-2,4-bis[(4-chlorobenzyl)oxy]-6,8-dioxabicyclo[3.2.1]octan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With barium(II) oxide In N,N-dimethyl-formamide at 60℃; for 3h; Inert atmosphere;	4.1.10. (1R,2S,3S,4R)-2,4-bis[(4-Chlorobenzyl)oxy]-6,8-dioxabicyclo[3.2.1]octan-3-ol 29 (1R,2S,3S,4R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (10 g, 61.7 mmol), 4-chlorobenzyl bromide (50.7 g, 247 mmol) and BaO (28 g, 185 mmol) in DMF (250 mL) was heated at 60 °C for 3 h. After cooling to 23 °C, the reaction was quenched with MeOH (130 mL) and the resulting mixture stirred for 30 min, diluted with CHCl3 (500 mL) and filtered through Celite. The filtrate was concentrated in vacuo and chromatographed (2:1 pentane: EtOAc) to give sugar 29 (17 g, 42.1 mmol, 68%) as an off-white, amorphous solid. 1H NMR (400 MHz, CDCl3) δ: 7.30-7.27 (8H, m), 5.45 (1H, s), 4.65 (2H, s), 4.63 (2H, s), 4.58 (1H, d, J=5.1 Hz), 3.85-3.83 (2H, m), 3.68 (1H, dd, J=7.5, 5.3 Hz), 3.32 (1H, d, J=4.0 Hz), 3.24 (1H, d, J=3.7 Hz), 2.33 (1H, d, J=4.9 Hz). 13C NMR (101 MHz, CDCl3) δ: 136.3, 136.2, 133.7, 133.6, 129.1 (2C), 129.0 (2C), 128.6 (4C), 101.1, 79.7, 79.4, 75.0, 71.3, 70.9, 70.4, 66.4. HRMS: (ES+) Calculated for C22H23Cl2NNaO5 [M+CH3CN+Na]+: 474.0851; Found: 474.0831. IR νmax/cm-1 (neat): 3474 br, 1492, 1089, 1015, 892, 807. [α]24D: -24.6 (c=1.1, CHCl3).

Reference： [1]Cookson, Rosa; White, Andrew J.P.; Barrett, Anthony G.M. [Tetrahedron, 2018, vol. 74, # 38, p. 5040 - 5048]

87
[ 98-59-9 ]
[ 498-07-7 ]
[ 3868-05-1 ]
[ 23643-29-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 46%	With pyridine In toluene at 0 - 20℃; for 23h; Inert atmosphere;
1: 46% 2: 40%	With pyridine In toluene at 0 - 20℃; for 21h; Inert atmosphere;
1: 40% 2: 46%	With pyridine In toluene at 0 - 20℃; for 23h; Inert atmosphere;

Reference： [1]Denavit, Vincent; St-Gelais, Jacob; Tremblay, Thomas; Giguère, Denis [Chemistry - A European Journal, 2019, vol. 25, # 39, p. 9272 - 9279]
[2]Denavit, Vincent; Giguère, Denis; St-Gelais, Jacob [Organic and biomolecular chemistry, 2020, vol. 18, # 20, p. 3903 - 3907]
[3]St-Gelais, Jacob; Côté, Émilie; Lainé, Danny; Johnson, Paul A.; Giguère, Denis [Chemistry - A European Journal, 2020, vol. 26, # 59, p. 13499 - 13506]

88
[ 492-61-5 ]
[ 67-47-0 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 51.5% 2: 8.3%	With sulfonic acid functionalized carbon coated on acid activated red mud In water; dimethyl sulfoxide at 180℃; for 0.5h; Microwave irradiation;	2.7. Experimental procedure for the microwave synthesis of 5-HMF The production of 5-HMF from D-glucose was performed on a CEM Discovermicrowave reactor under the DMSO/water solvent mixture. The required amount of D-glucose, DMSO, water, and catalyst was mixed inside a glass vessel (10 mL) by an in-built magnetic stirring facility of the microwave reactor. The glass vessel was designed to withstand the temperature of the reaction and the auto-generated pressure at the reaction temperature. The temperature of the reactant mixture was raised to the desired value at a fixed microwave power of 120 W. Once the reaction was completed, and the microwave temperature was cooled down to the atmospheric level, the product was taken out of the glass vessel and centrifuged to separate the liquid phase from the solid.

Reference： [1]Das, Bikashbindu; Mohanty, Kaustubha [Applied Catalysis A: General, 2021, vol. 622]

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CAS No. :	498-07-7	MDL No. :	MFCD00063248
Formula :	C₆H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TWNIBLMWSKIRAT-VFUOTHLCSA-N
M.W :	162.14	Pubchem ID :	2724705
Synonyms :	1,6-Anhydro-β-D-glucopyranose;1,6-Anhydro-β-D-glucose	Chemical Name :	(1R,2S,3S,4R,5R)-6,8-Dioxabicyclo[3.2.1]octane-2,3,4-triol

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	32.38
TPSA :	79.15 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.82 cm/s

Log Po/w (iLOGP) :	1.04
Log Po/w (XLOGP3) :	-2.15
Log Po/w (WLOGP) :	-2.18
Log Po/w (MLOGP) :	-1.94
Log Po/w (SILICOS-IT) :	-1.31
Consensus Log Po/w :	-1.31

[ CAS No. 498-07-7 ] {[proInfo.proName]}

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	0.51
Solubility :	524.0 mg/ml ; 3.23 mol/l
Class :	Highly soluble
Log S (Ali) :	1.02
Solubility :	1690.0 mg/ml ; 10.4 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	1.87
Solubility :	11900.0 mg/ml ; 73.6 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.87

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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[ CAS No. 498-07-7 ] {[proInfo.proName]}

Quality Control of [ 498-07-7 ]

Related Doc. of [ 498-07-7 ]

Product Details of [ 498-07-7 ]

Calculated chemistry of [ 498-07-7 ]

Physicochemical Properties

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Lipophilicity

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Application In Synthesis of [ 498-07-7 ]

[ 498-07-7 ] Synthesis Path-Downstream 1~88

Similar Product of [ 498-07-7 ]

Precautionary Statements-General

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Similar Product of
[ 498-07-7 ]