[ CAS No. 87-72-9 ] {[proInfo.proName]}

Name: 87-72-9|(3R,4S,5S)-Tetrahydro-2H-pyran-2,3,4,5-tetraol|98%
Brand: Ambeed
SKU: A395369
Price: 5.0 USD
Availability: InStock
Rating: 92 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 87-72-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 87-72-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 87-72-9 ]

SDS Specification

Alternatived Products of [ 87-72-9 ]

Product Details of [ 87-72-9 ]

CAS No. :	87-72-9	MDL No. :	MFCD00006609
Formula :	C₅H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	150.13	Pubchem ID :	-
Synonyms :		Chemical Name :	(3R,4S,5S)-Tetrahydro-2H-pyran-2,3,4,5-tetraol

Calculated chemistry of [ 87-72-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	29.77
TPSA :	90.15 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.59
Log Po/w (XLOGP3) :	-3.02
Log Po/w (WLOGP) :	-2.58
Log Po/w (MLOGP) :	-2.32
Log Po/w (SILICOS-IT) :	-1.7
Consensus Log Po/w :	-1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	1.13
Solubility :	2030.0 mg/ml ; 13.5 mol/l
Class :	Highly soluble
Log S (Ali) :	1.69
Solubility :	7340.0 mg/ml ; 48.9 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	2.23
Solubility :	25600.0 mg/ml ; 171.0 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.8

Safety of [ 87-72-9 ]

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:

Application In Synthesis of [ 87-72-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 87-72-9 ]
Downstream synthetic route of [ 87-72-9 ]

[ 87-72-9 ] Synthesis Path-Upstream 1~15

1
[ 87-72-9 ]
[ 67-64-1 ]
[ 114861-22-2 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 2, p. 475 - 478
[2] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 219 - 236
[3] Tetrahedron, 1998, vol. 54, # 44, p. 13529 - 13546
[4] Tetrahedron, 2008, vol. 64, # 23, p. 5551 - 5562
[5] Tetrahedron, 2008, vol. 64, # 9, p. 2090 - 2100
[6] Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6201 - 6204

2
[ 87-72-9 ]
[ 67-64-1 ]
[ 114861-22-2 ]

Yield	Reaction Conditions	Operation in experiment
52%	at 20℃; for 12 h;	To the suspension of L(-) xylose (19.15 g, 127.5 mmol) and MgSO4 (30.72 g,255.0 mmol) in acetone (190 mL) at room temperature was added concentrated H2SO4(1.9 mL). 12 After this time, the reaction mixture (all L - (-) - xylose consumed) wasfiltered and the combined solids were washed with acetone (2 times, 20 mL per wash).The yellow filtrate was neutralized to pH ~ 9 with NH4OH solution while stirring. Thesuspended solids were removed by filtration. The filtrate was concentrated to give thebis-acetonide intermediate as a yellow oil. The yellow oil was suspended in water (5mL) and the pH was adjusted from 9 to 2 with 1 N HCl in water. The reaction mixturewas stirred at room temperature for 12 hours. The resulting mixture was neutralized bythe addition of 25percent (w / w) K3PO4 in water until the pH was about 7. The mixture wasextracted with EtOAc. The organic layer was dried over MgSO4, filtered andconcentrated in vacuo. The crude product was purified by silica gel columnchromatography to give the title compound (12.63 g, 52percent) as a yellow oil.

Reference： [1] Patent: KR101770302, 2017, B1, . Location in patent: Paragraph 0331; 0332

3
[ 87-72-9 ]
[ 114861-22-2 ]

Reference： [1] Tetrahedron, 1988, vol. 44, # 15, p. 4721 - 4736

4
[ 87-72-9 ]
[ 67-64-1 ]
[ 131156-47-3 ]

Reference： [1] Patent: CN107722031, 2018, A, . Location in patent: Paragraph 0012

5
[ 87-72-9 ]
[ 67-64-1 ]
[ 131156-47-3 ]

Reference： [1] Tetrahedron, 1988, vol. 44, # 15, p. 4721 - 4736

6
[ 87-72-9 ]
[ 108-24-7 ]
[ 3068-31-3 ]

Reference： [1] Synthetic Communications, 2008, vol. 38, # 23, p. 4116 - 4124
[2] Journal of Carbohydrate Chemistry, 2006, vol. 25, # 7, p. 595 - 614
[3] Tetrahedron, 2014, vol. 70, # 39, p. 7032 - 7043

7
[ 87-72-9 ]
[ 3068-31-3 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 20, p. 3897 - 3900
[2] Tetrahedron Letters, 1996, vol. 37, # 50, p. 9093 - 9096
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 818 - 823
[4] Tetrahedron, 2011, vol. 67, # 5, p. 971 - 975
[5] Carbohydrate Research, 2012, vol. 364, p. 28 - 40
[6] Russian Journal of General Chemistry, 2017, vol. 87, # 3, p. 456 - 462[7] Zh. Obshch. Khim., 2017, vol. 87, # 3, p. 450 - 456,7
[8] Journal of Natural Products, 2017, vol. 80, # 6, p. 1798 - 1807
[9] Russian Journal of General Chemistry, 2016, vol. 86, # 13, p. 3002 - 3007[10] Zh. Obshch. Khim., 2016, vol. 25, # 3, p. 125 - 131,7

8
[ 87777-05-7 ]
[ 1532-97-4 ]
[ 87-72-9 ]

Reference： [1] Carbohydrate Research, 1993, vol. 250, # 1, p. 79 - 86

9
[ 87-72-9 ]
[ 3080-30-6 ]

Reference： [1] Nucleosides and Nucleotides, 1999, vol. 18, # 2, p. 187 - 195

10
[ 18604-54-1 ]
[ 87-72-9 ]
[ 97-53-0 ]
[ 498-05-5 ]
[ 18604-50-7 ]

Reference： [1] Bioscience, Biotechnology and Biochemistry, 2006, vol. 70, # 3, p. 691 - 698

11
[ 87-72-9 ]
[ 56-41-7 ]
[ 3658-77-3 ]
[ 27538-10-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 2, p. 531 - 536

12
[ 87-72-9 ]
[ 56-41-7 ]
[ 27538-10-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 2, p. 531 - 536

13
[ 97892-86-9 ]
[ 87-72-9 ]
[ 10257-28-0 ]
[ 6556-12-3 ]
[ 631-01-6 ]

Reference： [1] Phytochemistry (Elsevier), 1987, vol. 26, # 1, p. 229 - 236

14
[ 87-72-9 ]
[ 1103738-17-5 ]

Reference： [1] Patent: KR101770302, 2017, B1,

15
[ 87-72-9 ]
[ 1103738-19-7 ]

Reference： [1] Patent: KR101770302, 2017, B1,

[ 87-72-9 ] Synthesis Path-Downstream 1~55

1
[ 67-56-1 ]
[ 87-72-9 ]
[ 449173-64-2 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With hydrogenchloride In water at 63 - 65℃;	9.1 Preparation of 1-O-methyl-L-arabinoside At room temperature, To a 4-fold mass of saturated hydrogen chloride in methanol was added L-arabinose. The mixture was heated to 63 ° C to 65 ° C for 2 to 4 hours and cooled to room temperature. The solution was concentrated to 1/2 of the original volume to give a suspension. The solid precipitate was filtered off and the liquid was concentrated to 1/4 of the original volume. The solid precipitate was filtered off and all precipitates were washed with 0.5 times the mass of methanol and dried to give 1-methyl-L-arabinoside, 90.3%.
	With hydrogenchloride at 80℃; for 1.5h; Yield given;
	With Dowex-50 (H⁺)

	In methanol at 60℃;
	With hydrogenchloride at 80℃; for 14h;

Reference： [1]Current Patent Assignee: HE, SUI QING;LI, AI ZHEN;SHI, XIN JIAN;TONG, CHENG SONG;WANG, HAO - CN102153600, 2016, B Location in patent: Paragraph 0254-0259
[2]Doares, Steven H.; Albersheim, Peter; Darvill, Alan G. [Carbohydrate Research, 1991, vol. 210, p. 311 - 317]
[3]Tsuda; Kaneda; Yasufuku; Shimizu [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 8, p. 2123 - 2134]
[4]Motoki; Morita; Kobayashi; Uchida; Akimoto; Fukushima; Koezuka [Biological and Pharmaceutical Bulletin, 1995, vol. 18, # 11, p. 1487 - 1491]
[5]Gutierrez, Marcelino; Capson, Todd L.; Guzman, Hector M.; Gonzalez, Jose; Ortega-Barria, Eduardo; Quinoa, Emilio; Riguera, Ricardo [Journal of Natural Products, 2006, vol. 69, # 10, p. 1379 - 1383]

2
[ 87-72-9 ]
[ 1124-32-9 ]
[ 2001-96-9 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6279 - 6282

3
[ 87-72-9 ]
[ 453-17-8 ]
[ 532-20-7 ]
[ 141-46-8 ]
[ 78-98-8 ]

Reference： [1]Carbohydrate Research,1991,vol. 217,p. 71 - 86

4
[ 87-72-9 ]
[ 10326-41-7 ]
[ 453-17-8 ]
[ 532-20-7 ]
[ 78-98-8 ]

Reference： [1]Carbohydrate Research,1991,vol. 217,p. 71 - 86

5
[ 532-20-7 ]
[ 98-01-1 ]
[ 87-72-9 ]
[ 453-17-8 ]
[ 78-98-8 ]

Reference： [1]Carbohydrate Research,1991,vol. 217,p. 71 - 86

6
[ 87-72-9 ]
[ 108-24-7 ]
[ 123163-97-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; 4-dimethylaminopyridine In dichloromethane at 20℃; for 24h;
100%	With perchloric acid In dichloromethane at 0℃; for 1h;	4.2.2.1 Synthesis of acetylated sugars General procedure: Acetylation of sugars were performed according to the literature reports by taking sugars in 50mL round bottom flask in Dichloromethane with stirring bar magnet. Then, Acetic anhydride (1.2eq. per OH) and Perchloric acid (0.1eq.) were added sequentially at 0°C. The reaction mixture was stirred at same temperature until TLC indicated the complete conversion of starting material [34].
100%	With perchloric acid In dichloromethane at 0℃; for 1h;	4.2.2.1 Synthesis of acetylated sugars General procedure: Acetylation of sugars were performed according to the literature reports by taking sugars in 50mL round bottom flask in Dichloromethane with stirring bar magnet. Then, Acetic anhydride (1.2eq. per OH) and Perchloric acid (0.1eq.) were added sequentially at 0°C. The reaction mixture was stirred at same temperature until TLC indicated the complete conversion of starting material [34].

99%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	1.e Synthesis of L-Arabinose Tetraacetate To a stirred solution of L-arabinose (5.00 g, 33.3 mmol), Ac20 (14.14 mL, 149.9 mmol)and Et3N (21.99 mL, 156.5 mmol) in CH2C12 (60 mL) at 0 °C was added DMAP (101 mg, 0.83mmol). The resulting solution was stirred at rt for 12 h and washed with ice water (200 mLx3). The reaction was quenched with a solution of saturated NaHCO3 and the aqueous phase was extracted with CH2C12 (100 mLx3). The combined organic phase was washed with brine and dried over Na2SO4. The filtrate was concentrated under vacuum affording a sticky residue LH arabinose tetraacetate (10.48 g, 99%), which was used directly in next step without further purification.
96%	With lanthanum trifluoromethanesulphonate at 20℃; for 0.416667h;
95%	With iodine at 20℃; for 1h;
94%	With pyridine; 4-dimethylaminopyridine at 0 - 20℃; Inert atmosphere;	Compound 219: To a solution of L-(+)-Arabinose 8 (1.2 g, 7.99 mmol) in pyridine (12 mL) was added acetic anhydride (7.6 mL, 80.40 mmol) and 4-(dimethylamino)pyridine (146.5 mg, 1.20 mmol) at 0 °C under N2. The mixture was stirred at ambient temperature overnight; poured into sat. aq. NaHCCb; stirred for 30 min; and extracted twice with EtOAc. The combined organic extracts were washed with sat. aq. NaHCCT and water. The organic extract was dried with Na2S04; filtered; and concentrated. The residue was purified by column chromatography (silica gel, eluting with 0% to 40% acetone in hexanes) to give compound 219 (2.4 g, 94% yield) as a clear viscous oil. m/z = 259.1 (M-OAc)
93%	With pyridine at 140℃; Inert atmosphere;
91%	In acetonitrile for 0.0111111h; microwave irradiation;
70%	With triethylammonium acetate at 20℃; for 3h;	Typical Procedure General procedure: To a stirred solution of 2-naphthol (0.2 mmol) in TEAA(2 ml), was added acetic anhydride (0.22 mmol). The solutionwas stirred for 3 hours at room temperature. After consumptionof starting material (TLC monitoring, ethyl acetate/hexane, 2:8), the product formed was diluted with 1 mlH2O and extracted with 3 x 2 ml ether. The combined organiclayer was separated, dried (Na2SO4), and evaporatedunder reduced pressure to afford the desired product. 1H and13C NMR spectra were in full accordance with the structureproposed. The water in the aqueous layer was distilled under reduced pressure leaving behind the TEAA which was furtherrecycled.
35%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 15℃; for 16h;	138 Example 138: [(35,45,5R)-4,5,6-triacetoxytetrahydropyran-3-yl] acetate To a solution of (3R,45,55)-tetrahydropyran-2,3,4,5-tetrol (2 g), triethylamine (10.91 g) and 4- dimethylaminopyridine (0.1 63 g,) in CH2CI2 (20 mL) was added acetyl acetate (8.72 g), and the mixture was stirred at 15°C for 16 h. The solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (petroleum ether / ethyl acetate gradient) to give [(3S,4S,5R)-4,5,6- triacetoxytetrahydropyran-3-yl] acetate (1.5 g, 35% yield) as a yellow solid. LCMS: 341.1 (M÷Na) 1H NMR (400 MHz, CDCI3): O 6.348 (d, 1H), 5.379 - 5.347 (m, 3H), 4.061 (d, 1H), 3.824 (m, 1H), 2.139 (s, 6H), 2.039 (s, 6H) ppm
	With pyridine Ambient temperature;
	With hydrogen bromide In glacial acetic acid for 4h; Ambient temperature;
	With pyridine; 4-dimethylaminopyridine at 0 - 20℃;
	With pyridine at 20℃; for 4h;
	With pyridine
35 g	With pyridine at 0℃; for 48h;
	With pyridine at 0℃; for 16h;
	With pyridine
	at 20℃; for 0.25h;
	With perchloric acid optical yield given as %de;
	With iodine
	With indium trifluoromethanesulfonate In neat (no solvent) for 0.5h; Milling;
	With pyridine at 23℃;
	With pyridine; 4-dimethylaminopyridine In dichloromethane
	With pyridine
	With pyridine; glacial acetic acid at 90℃; for 6h;	2. General procedure for preparation of 1-bromo glycosyl donor General procedure: To a solution of reducing sugars (4 mmol) in anhydrous pyridine (10mL) was added Ac2O (20 mL)and AcOH (3 mL) at room temperature. After stirred to react for 6h at 90 C, the reaction mixturewas quenched with MeOH and was concentrated under reduced pressure. The resulting solutionwas diluted with EtOAc and washed with 1M HCl, saturated NaHCO3 and water successively. Theorganic layer was dried over anhydrous Na2SO4 and then concentrated to dryness under reducedpressure. The peracetylated sugars (a-o) were obtained and used without further purification.
	Stage #1: L-arabinopyranose With pyridine at 0℃; Sealed tube; Stage #2: acetic anhydride at 0℃; for 5h;	7 Synthesis of Tetra-O-acetyt-L-Arabinose (28) To a 500-mL three-neck RBF equipped with guard-tube and stopper, were added 27 (40.0 g, 0.266 mol), pyridine (200 mL) and cooled it at 0 °C. Acetic anhydride (200 mL) was added dropwise to the above mixture at 0 °C. The resulting reaction mixture was stirred at 0 °C for 5 h. After consumption of starting materials, as judged by TLC (5:5, EtOAc: Hexane), reaction mixture was poured into ice water (500 mL) and ether was added (200 mL). Organic layer was separated and aqueous layer was extracted with ether (2 x 250 mL). Organic layers were combined and washed with saturated cupric salt solution tillfree from pyridine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give sticky solid compound 28.‘H-NMR (300 MHz, CDC13): 6 = 6.27 (d, 1H, J = 3.6 Hz), 5.70 (t, 1H, J = 9 Hz), 5.06 (m, 2H), 3.97 (dd, TH, J =6.0, 11.1 Hz), 3.72 (t, 1H, J = 11.0 Hz), 2.18 (s, 3H), 2.07(s, 6H), 2.03 (s, 3H).
	With pyridine at 20℃;	General procedure for the synthesis of Sugar Azides (4a-l) General procedure: Sugar azides were synthesised by the reported procedures in the literature based on Bertho’s method. Firstly, Sugars are acetylated adding an excess amount of acetic anhydride in anhydrous pyridine and the reaction mixture is allowed to stir overnight at room temperature. Concentrate the reaction mixture under reduced pressure and co-evaporate several times with Toluene to remove (traces of) Pyridine. Purify the residue with column chromatography with hexane:EtOAc (6:4). This should give you 95-97 % yield of your Alfa/beta product in 3:1 ratio. Pentacetylated sugars made to react with HBr in AcOH (33 %) at 0 °C. Then, stir the reaction mass at room temperature for 2 hours. The reaction mass was diluted with dichloromethane (40 ml) and water. The organic layer was separated and the aqueous layer extracted with dichloromethane (2 x 20 ml). The combined organic layers were dried (anhydrous Na2SO4) and evaporated under reduced pressure to afford a desired product glycosyl bromide in very high yield (~98 %). Pentacetylated glycosyl bromide was then refluxed for 2h at 100 °C with NaN3 in the presence of PTC to yield corresponding glycosyl azides, which was subjected to column chromatography (silica gel, 60-120 mesh, eluent; n-hexane/EtOAc gradient) to afford pure products (4a-l).
	With pyridine; 4-dimethylaminopyridine at 20℃;
	With perchloric acid at 0 - 20℃;
	With pyridine for 5h;
	In pyridine at 0 - 15℃; for 28h;
	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 0℃; for 12h; Inert atmosphere;

Reference： [1]Alcaro; Arena; Neri; Ottana; Ortuso; Pavone; Vigorita [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 7, p. 1781 - 1791]
[2]Kaur Gulati, Harmandeep; Choudhary, Sushil; Kumar, Nitish; Ahmed, Ajaz; Bhagat, Kavita; Vir Singh, Jatinder; Singh, Atamjit; Kumar, Ajay; Singh Bedi, Preet Mohinder; Singh, Harbinder; Mukherjee, Debaraj [Bioorganic Chemistry, 2022, vol. 118]
[3]Kaur Gulati, Harmandeep; Choudhary, Sushil; Kumar, Nitish; Ahmed, Ajaz; Bhagat, Kavita; Vir Singh, Jatinder; Singh, Atamjit; Kumar, Ajay; Singh Bedi, Preet Mohinder; Singh, Harbinder; Mukherjee, Debaraj [Bioorganic Chemistry, 2022, vol. 118]
[4]Current Patent Assignee: THE UNIVERSITY OF IOWA - WO2017/100153, 2017, A1 Location in patent: Page/Page column 20; 21
[5]Dasgupta, Somnath; Rajput, Vishal Kumar; Roy, Bimalendu; Mukhopadhyay, Balaram [Journal of Carbohydrate Chemistry, 2007, vol. 26, # 2, p. 91 - 106]
[6]Mukhopadhyay, Balaram; Kartha, K.P. Ravindranathan; Russell, David A.; Field, Robert A. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7758 - 7760]
[7]Current Patent Assignee: REATA PHARMACEUTICALS, INC. - WO2019/222269, 2019, A1 Location in patent: Page/Page column 174; 246
[8]Blaszczyk, Stephanie A.; Xiao, Guozhi; Wen, Peng; Hao, Hua; Wu, Jessica; Wang, Bo; Carattino, Francisco; Li, Ziyuan; Glazier, Daniel A.; McCarty, Bethany J.; Liu, Peng; Tang, Weiping [Angewandte Chemie - International Edition, 2019, vol. 58, # 28, p. 9542 - 9546][Angew. Chem., 2019, vol. 131, # 28, p. 9642 - 9646,5]
[9]Das, Saibal Kumar; Reddy, K. Anantha; Krovvidi, V. L. Narasimha Rao; Mukkanti [Carbohydrate Research, 2005, vol. 340, # 7, p. 1387 - 1392]
[10]Lafuente, Leticia; Díaz, Gisela; Bravo, Rodolfo; Ponzinibbio, Agustín [Letters in Organic Chemistry, 2016, vol. 13, # 3, p. 195 - 200]
[11]Current Patent Assignee: FLAGSHIP PIONEERING INC - WO2018/226732, 2018, A1 Location in patent: Page/Page column 137; 138
[12]Miller, Vaughn P.; Yang, Ding-yah; Weigel, Theresa M.; Han, Oksoo; Liu, Hung-wen [Journal of Organic Chemistry, 1989, vol. 54, # 17, p. 4175 - 4188]
[13]Shull, Brian K.; Wu, Zhijun; Koreeda, Masato [Journal of Carbohydrate Chemistry, 1996, vol. 15, # 8, p. 955 - 964]
[14]Chen, Xiao-Tao; Zhou, Bishan; Bhattacharya, Samit K.; Gutteridge, Clare E.; Pettus, Thomas R. R.; Danishefsky, Samuel J. [Angewandte Chemie - International Edition, 1998, vol. 37, # 6, p. 789 - 792] Chen, Xiao-Tao; Bhattacharya, Samit K.; Zhou, Bishan; Gutteridge, Clare E.; Pettus, Thomas R. R.; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1999, vol. 121, # 28, p. 6563 - 6579]
[15]Sznaidman, Marcos L.; Almond, Merrick R.; Pesyan, Amir [Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 2, p. 155 - 163]
[16]Tamaruya, Yoko; Suzuki, Masato; Kamura, Goshu; Kanai, Motomu; Hama, Kotaro; Shimizu, Kumiko; Aoki, Junken; Arai, Hiroyuki; Shibasaki, Masakatsu [Angewandte Chemie - International Edition, 2004, vol. 43, # 21, p. 2834 - 2837]
[17]Ple, Karen; Chwalek, Martin; Voutquenne-Nazabadioko, Laurence [European Journal of Organic Chemistry, 2004, # 7, p. 1588 - 1603]
[18]Iriarte Capaccio, Christian A.; Varela, Oscar [Journal of Organic Chemistry, 2002, vol. 67, # 22, p. 7839 - 7846]
[19]Wahler, Denis; Boujard, Olivier; Lefèvre, Fabrice; Reymond, Jean-Louis [Tetrahedron, 2004, vol. 60, # 3, p. 703 - 710]
[20]Roy, Bimalendu; Dasgupta, Somnath; Kumar Rajput, Vishal; Mukhopadhyay, Balaram [Journal of Carbohydrate Chemistry, 2008, vol. 27, # 1, p. 1 - 9]
[21]Location in patent: body text Colinas, Pedro Alfonso; Tempera, Carlos Agustin; Rodriguez, Oscar Mariano; Bravo, Rodolfo Daniel [Synthesis, 2009, # 24, p. 4143 - 4148]
[22]Location in patent: scheme or table Jarman, Bevan P.; Nicholson, Brian K. [Journal of Organometallic Chemistry, 2012, vol. 702, p. 1 - 9]
[23]Kumar, Vajinder; Taxak, Nikhil; Jangir, Ramniwas; Bharatam, Prasad V.; Kartha, K. P. Ravindranathan [Journal of Organic Chemistry, 2014, vol. 79, # 8, p. 3427 - 3439]
[24]Mancini, Ross S.; McClary, Corey A.; Anthonipillai, Stefi; Taylor, Mark S. [Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8501 - 8510]
[25]Current Patent Assignee: UNIVERSITY SYSTEM OF OHIO - WO2015/153653, 2015, A1 Location in patent: Sheet 9/20
[26]Yu, Wenbo; Jiang, Luxia; Shen, Chao; Zhang, Pengfei [Drug Development Research, 2016, p. 319 - 325] Kremenko; Kharitonov, Yu. V.; Shul’ts [Russian Journal of Organic Chemistry, 2017, vol. 53, # 1, p. 35 - 46][Zh. Org. Khim., 2017, vol. 53, # 1, p. 42 - 52,11]
[27]Li, Xiao-san; Ren, Yi-chang; Bao, Yu-zhou; Liu, Jie; Zhang, Xiao-kun; Zhang, You-wei; Sun, Xue-Long; Yao, Xin-sheng; Tang, Jin-Shan [European Journal of Medicinal Chemistry, 2018, vol. 145, p. 252 - 262]
[28]Current Patent Assignee: GODAVARI BIOREFINERIES - WO2018/193476, 2018, A2 Location in patent: Page/Page column 58; 59
[29]Nerella, Srinivas; Kankala, Shravankumar; Gavaji, Brahmeshwari [Natural Product Research, 2021, vol. 35, # 1, p. 9 - 16]
[30]Su, Yangqing; Meng, Lingkuan; Sun, Jiaqi; Li, Weijia; Shao, Liang; Chen, Kexuan; Zhou, Demin; Yang, Fan; Yu, Fei [European Journal of Medicinal Chemistry, 2019, vol. 182]
[31]Zhang, Peng; Ma, Jing; Zhang, Qianqian; Jian, Shandong; Sun, Xiaoliang; Liu, Bobo; Nie, Liqin; Liu, Meiyan; Liang, Songping; Zeng, Youlin; Liu, Zhonghua [Journal of Medicinal Chemistry, 2019, vol. 62, # 17, p. 7857 - 7873]
[32]Fan, Zhanfang; Guo, Chun; Hou, Zhuang; Li, Chuanchao; Lin, Bin; Liu, Yang; Liu, Yichuang; Wang, Yitong; Zhang, Miao [Journal of Enzyme Inhibition and Medicinal Chemistry, 2020, vol. 35, # 1, p. 383 - 390]
[33]Nakamura, Sho; Sayama, Misa; Uwamizu, Akiharu; Jung, Sejin; Ikubo, Masaya; Otani, Yuko; Kano, Kuniyuki; Omi, Jumpei; Inoue, Asuka; Aoki, Junken; Ohwada, Tomohiko [Journal of Medicinal Chemistry, 2020, vol. 63, # 17, p. 9990 - 10029]
[34]Geng, Mingyu; Yu, Biao; Zhu, Dapeng [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]

7
[ 97892-86-9 ]
[ 87-72-9 ]
[ 10257-28-0 ]
[ 6556-12-3 ]
[ 631-01-6 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 229 - 236

8
[ 84954-92-7 ]
[ 87-72-9 ]
[ 4510-34-3 ]
[ 34047-83-1 ]
[ 4407-36-7 ]

Reference： [1]Chemistry of Natural Compounds,1982,vol. 18,p. 685 - 688
Khimiya Prirodnykh Soedinenii,1982,vol. 18,p. 723 - 727

9
[ 87-72-9 ]
[ 67-64-1 ]
[ 131156-47-3 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 4721 - 4736

10
3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-gucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1-3>)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-gucopyranoside [ No CAS ]
[ 87-72-9 ]
[ 10257-28-0 ]
[ 6556-12-3 ]
[ 73-34-7 ]
[ 73-34-7 ]
[ 631-01-6 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 229 - 236

11
diurnoside [ No CAS ]
[ 87-72-9 ]
[ 2280-44-6 ]
[ 10257-28-0 ]
[ 77-60-1 ]

Reference： [1]Phytochemistry,1993,vol. 34,p. 511 - 515

12
3-(α-L-arabinopyranosyloxy)-3-phenylpropionitrile [ No CAS ]
[ 87-72-9 ]
[ 3480-87-3 ]

Reference： [1]Phytochemistry,1981,vol. 20,p. 1857

13
primeveroside du 4-(-2-aminoethyl)phenol [ No CAS ]
[ 87-72-9 ]
[ 2280-44-6 ]
[ 60-19-5 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 1251 - 1252

14
[ 106-48-9 ]
[ 2001-96-9 ]
[ 87-72-9 ]
[ 100-02-7 ]
[ 3325-47-1 ]

Reference： [1]Carbohydrate Research,1982,vol. 100,p. 221 - 234

15
[ 150-76-5 ]
[ 2001-96-9 ]
[ 87-72-9 ]
[ 100-02-7 ]
[ 13299-09-7 ]

Reference： [1]Carbohydrate Research,1982,vol. 100,p. 221 - 234

16
[ 2001-96-9 ]
[ 87-72-9 ]
[ 100-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water; In aq. buffer; at 45℃; for 0.166667h;pH 7.5;Kinetics;	The standard activity assay used pNP beta-D-Xylp as substrate. Release of p-nitrophenol (pNP) was measured by continuous monitoring at 401 nm. Reactions were performed in 50 mM Tris-HCl, pH 7.5 and the substrate concentration was 5 mM. Assays were performed at 45 C for 10 min. Activity was determined by using a standard calibration curve for pNP (epsilon = 12514M-1cm-1). One unit of beta-xylosidase activity was defined as the amount of enzyme releasing 1 mumol of pNP per minute. Kinetic parameters Km and kcat were determined using variable substrate concentrations (1-75 mM) in the standard assay. Data were calculated from triplicate assays. Kinetic parameters were derived from Michaelis-Menten representations using the SigmaPlot 2000 software (version 6.1 with Enzyme Kinetics module 1.0; SPSS Science, Paris, France).

Reference： [1]Carbohydrate Research,1982,vol. 100,p. 221 - 234
[2]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 96,p. 21 - 26

17
[ 87-72-9 ]
[ 56-41-7 ]
[ 3658-77-3 ]
[ 27538-10-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 531 - 536

18
[ 87-72-9 ]
[ 56-41-7 ]
[ 27538-10-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 531 - 536

19
[ 87-72-9 ]
[ 3658-77-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 531 - 536

20
[ 87-72-9 ]
[ 56-40-6 ]
[ 3658-77-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 531 - 536

21
[ 87-72-9 ]
[ 19322-27-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1998,vol. 46,p. 235 - 241

22
[ 87-72-9 ]
[ 56-40-6 ]
[ 19322-27-1 ]
2-acetyl-6-(hydroxymethyl)-5,6-dihydro-4H-pyridinone [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,1999,vol. 47,p. 438 - 443

23
[ 87-72-9 ]
PhCOX, AcOY [ No CAS ]
[ 3080-30-6 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 693 - 695

24
[ 87-72-9 ]
[ 3080-30-6 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 187 - 195

25
L-(+)-arabinose [ No CAS ]
[ 149-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: HCl 2: sulphuric acid 3: 66 percent 4: triphenylphosphine, propylene oxid / CH₂Cl₂ 5: 60 percent / HClO₄ / H₂O; tetrahydrofuran / 1.25 h / Heating 6: 65 percent / trifluoroacetic acid anhyride, triethyl amine / tetrahydrofuran / 0.17 h / 25 °C / dry THF used
	Multi-step reaction with 7 steps 1: HCl 2: sulphuric acid 3: 66 percent 4: triphenylphosphine, propylene oxid / CH₂Cl₂ 5: 33 percent / HClO₄ / H₂O; tetrahydrofuran / 1.25 h / Heating 6: Pd-C / cyclohexene / further solvents 7: 65 percent / trifluoroacetic acid anhyride, triethyl amine / tetrahydrofuran / 0.17 h / 25 °C / dry THF used

Reference： [1]Gill, G. Bryon; Pattenden, Gerald; Stapleton, Alan [Tetrahedron Letters, 1988, vol. 29, # 23, p. 2875 - 2878]
[2]Gill, G. Bryon; Pattenden, Gerald; Stapleton, Alan [Tetrahedron Letters, 1988, vol. 29, # 23, p. 2875 - 2878]

26
[ 87-72-9 ]
[ 87-72-9 ]
[ 50-99-7 ]
[ 59-23-4 ]
[ 488-82-4 ]
[ 87-99-0 ]
[ 50-70-4 ]
[ 608-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;ruthenium chloride supported on zirconia (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 40percent; chlorine content 50 ppm); In water; at 60℃; under 36778.6 Torr; for 100h;Product distribution / selectivity;	EXAMPLE 6The procedure of example 4 was repeated except that the sugar containing 80 % xylose, 9 % arabinose, 5 % galactose, and 6 % glucose was used aes a reactant. After the reaction was conducted for 100 hours, the average purities of hydrogenated sugar alcohols were 79.8 %, 9.2 %, 5 %, and 5.9 % for xylitol, arabitol, galactitol, and sorbitol, respectively. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.

Reference： [1]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 13-14

27
[ 87-72-9 ]
[ 87-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;ruthenium chloride supported on silica (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 45percent; chlorine content 54 ppm); In water; at 50 - 60℃; under 36778.6 Torr; for 100h;Product distribution / selectivity;	EXAMPLE lRuthenium chloride was uniformly supported on silica pellets having a size of 2 mm so that a ruthenium content was 3 wt%, dried at 110C for 6 hours,. and calcined in a nitrogen atmosphere at 500C for 5 hours to produce a ruthenium catalyst having the ruthenium dispersion of 45 % and a chlorine content of 54 ppm. 2 g of catalyst thus produced was packed into a fixed-bed tubular reactor made of stainless steel, and reduction was subsequently conducted at 350C for 6 hours in the presence of hydrogen flowing at a rate of 50 cc per minute. After the reduction was completed, the flow rate of hydrogen was controlled so that it was 6 times the amount of xylose used, expressed aes a molar ratio. After a temperature and pressure of the reactor were set to 50C and 50 kg/cm2, a reactant was fed at a weight hourly space velocity (WHSV) of 0.18 h"1 (on the basis of xylose) to initiate a reaction. 40wt% solution of xylose dissolved in distilled water was used aes the reactant, and the product was analyzed using liquid chromatography provided with a refractive Index detector. After the reaction was carried out for 100 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.9 %. Reactivity was not reduced even though the reaction was continuously performed for 3,000 hours or more.EXAMPLE 2The procedure of example l was repeated except that the reaction temperature was 60C and the WHSV was 0.24 h"1. After the reaction was conducted for 100 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.8 %. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.
	With hydrogen;ruthenium chloride supported on alumina (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 3.0percent; chlorine content 54 ppm); In water; at 50℃; under 36778.6 Torr; for 10 - 48h;Product distribution / selectivity;	COMPARATIVE EXAMPLE 2The procedure of example l was repeated except that 3 wt% of ruthenium was dispersed with the ruthenium dispersion of 3.0 % in an alumina carrier, which had 85.3 % mesopores of 2 -50 nm and 14.7 % macropores of 50 - 10,000 nm based on a pore volume thereof, to produce a catalyst. After the reaction was conducted for 10 hours, the average conversion of xylose was 82.1 % and the selectivity of xylitol was 99.8 %. The catalyst was deactivated over time and the conversion of xylose was 72.1 % after 48 hours.
	With hydrogen;ruthenium chloride supported on silica (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 2.8percent; chlorine content 54 ppm); In water; at 50℃; under 36778.6 Torr; for 100h;Product distribution / selectivity;	COMPARATIVE EXAMPLE lThe procedure of example l was repeated except that silica was used aes a carrier to produce 3 wt% of ruthenium catalyst having the ruthenium dispersion 2.8 %. After the reaction was conducted for 100 hours, the average conversion of xylose was 82.1 % and the selectivity of xylitol was 99.9 %. The production efficiency per time was reduced because the dispersion was low.

	With hydrogen;ruthenium chloride supported on silica (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion >= 10percent; chlorine content 1000 ppm); In water; at 50℃; under 36778.6 Torr; for 20 - 270h;Product distribution / selectivity;	COMPARATIVE EXAMPLE 3The procedure of example l was repeated except that silica was used aes a carrier to produce a 3 wt% rutheniumcatalyst having the ruthenium dispersion of 10 % or more and a chlorine content of 1,000 ppm. After the reaction was conducted for 20 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.9 %. The catalyst was slowly deactivated over time and the conversion of xylose was 96.3 % after 270 hours.
	With hydrogen;ruthenium chloride supported on silica/zirconia (90:10 wtpercent) (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 42percent; chlorine content 60 ppm); In water; at 60℃; under 36778.6 Torr; for 100h;Product distribution / selectivity;	EXAMPLE 7The procedure of example 4 was repeated except that silica-zirconia consisting of 90 wt% silica and 10 wt% zirconia was used aes a carrier to produce a 3 wt% ruthenium catalyst having the ruthenium dispersion of 42 % and a chlorine content of 60 ppm. After the reaction was conducted for 100 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.8 %. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.
	With hydrogen;ruthenium chloride supported on zirconia (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 40percent; chlorine content 50 ppm); In water; at 60℃; under 36778.6 Torr; for 100h;Product distribution / selectivity;	EXAMPLE 4Ruthenium Chloride was uniformly supported on zirconia pellets having a size of 3 mm, so that a ruthenium content was 3 wt%, dried at 110C for 6 hours, and calcined under a nitrogen atmosphere at 500C for 5 hours to produce a ruthenium catalyst having the ruthenium dispersion of 40 % and a chlorine content of 50 ppm. 6 g of catalyst thus produced were packed into a fixed-bed tubular reactor made of stainless steel, and the reduction was subsequently conducted at 350C for 6 hours in the presence of hydrogen flowing at a rate of 50 cc per minute. After the reduction was completed, the flow rate of hydrogen was controlled so that it was 6 times the amount of xylose used, expressed aes a molar ratio. After the temperature and pressure of the reactor were set to 60C and 50 kg/cm2, a reactant was fed at the WHSV of 0.10 h'1 (on the basis of xylose) to initiate a reaction. 40 wt% solution of xylose dissolved in distilled water was used aes the reactant, and the product was analyzed using liquid Chromatograph provided with a refractive Index detector. After the reaction was conducted for 100 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.8 %. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.
	With hydrogen;ruthenium chloride supported on zirconia (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion >=10percent; chlorine content 1000 ppm); In water; at 60℃; under 36778.6 Torr; for 20 - 270h;Product distribution / selectivity;	EXAMPLE 4Ruthenium Chloride was uniformly supported on zirconia pellets having a size of 3 mm, so that a ruthenium content was 3 wt%, dried at 110C for 6 hours, and calcined under a nitrogen atmosphere at 500C for 5 hours to produce a ruthenium catalyst having the ruthenium dispersion of 40 % and a chlorine content of 50 ppm. 6 g of catalyst thus produced were packed into a fixed-bed tubular reactor made of stainless steel, and the reduction was subsequently conducted at 350C for 6 hours in the presence of hydrogen flowing at a rate of 50 cc per minute. After the reduction was completed, the flow rate of hydrogen was controlled so that it was 6 times the amount of xylose used, expressed aes a molar ratio. After the temperature and pressure of the reactor were set to 60C and 50 kg/cm2, a reactant was fed at the WHSV of 0.10 h'1 (on the basis of xylose) to initiate a reaction. 40 wt% solution of xylose dissolved in distilled water was used aes the reactant, and the product was analyzed using liquid Chromatograph provided with a refractive Index detector. After the reaction was conducted for 100 hours, the average conversion of xylose was 99.9 % and the selectivity of xylitol was 99.8 %. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.

Reference： [1]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 11-12
[2]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 15
[3]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 15
[4]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 15-16
[5]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 14
[6]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 12-13
[7]Patent: WO2005/21475,2005,A1 .Location in patent: Page/Page column 16
[8]RSC Advances,2013,vol. 3,p. 25997 - 26004
[9]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9727 - 9733

28
[ 41910-64-9 ]
[ 87-72-9 ]
4-chloro-2,3-dihydro-1-β-D-xylopyranosyl-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178

29
[ 87-72-9 ]
[ 52537-00-5 ]
C₁₃H₁₆ClNO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178

30
[ 87-72-9 ]
[ 86626-38-2 ]
C₁₃H₁₆BrNO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178

31
[ 87-72-9 ]
[ 65826-95-1 ]
C₁₄H₁₉NO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178

32
[ 87-72-9 ]
[ 84807-26-1 ]
C₁₃H₁₆N₂O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178

33
3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-α-L-rhamnopyranosyl-(1->2)-[α-L-arabinopyranosyl-(1->4)]-β-D-fucopyranosyl ester [ No CAS ]
[ 87-72-9 ]
[ 10257-28-0 ]
[ 6556-12-3 ]
[ 73-34-7 ]
[ 87-72-9 ]
[ 73-34-7 ]
[ 631-01-6 ]

Reference： [1]Carbohydrate Research,2010,vol. 345,p. 68 - 73

34
3-O-β-D-galactopyranosyl-(1->2)-[α-L-arabinopyranosyl-(1->3)]-β-D-glucopyranosyl quillaic acid 28-O-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-[β-D-glucopyranosyl-(1->3)]-α-L-rhamnopyranosyl-(1->2)-[α-L-rhamnopyranosyl-(1->4)]-β-D-fucopyranosyl ester [ No CAS ]
[ 87-72-9 ]
[ 2280-44-6 ]
[ 10257-28-0 ]
[ 73-34-7 ]
[ 87-72-9 ]
[ 73-34-7 ]
[ 631-01-6 ]

Reference： [1]Carbohydrate Research,2010,vol. 345,p. 68 - 73

35
[ 87-72-9 ]
[ 2001-96-9 ]
[ 552-71-6 ]

Reference： [1]Carbohydrate Research,2011,vol. 346,p. 421 - 429

36
[ 87-72-9 ]
[ 2001-96-9 ]
β-D-xylopyranosyl-(1->4)-D-lyxopyranoside [ No CAS ]

Reference： [1]Carbohydrate Research,2011,vol. 346,p. 421 - 429

37
[ 1374792-02-5 ]
[ 87-72-9 ]
[ 2280-44-6 ]
[ 10257-28-0 ]
[ 77-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 100℃; for 4h;	General procedure; Compounds 1 and 2 (2 mg) were separately heated with 10% aqueous HCl (2 mL) in a sealed tube at 100 C for 4 h. The aglycone was extracted with diethyl ether and analyzed by TLC and comparison of its Rf value with that of an authentic sample using system B. The aqueous layer was neutralized with N,N-dioctylamine (10% in CHCl3). After evaporation of the solvent in vacuo, the sugars were initially identified by TLC and comparison of their Rf values with those of authentic samples using system C. In order to confirm the nature of the sugar residue, the latter was heated with pyridine (800 muL) and N-(trimethylsilyl)imidazole (200 muL) in a sealed tube at 60 C for 1 h. The reaction was quenched by the addition of H2O (3 mL) and cyclohexane (3 mL) and the mixture was partitioned between the aqueous and the organic layer. After evaporation of the organic layer in vacuo, the residue was analyzed by GC-MS and comparison of the retention times of the TMSi derivatives of the monosaccharides with those of authentic trimethylsilylated sugars. Thus, the sugar residues of compounds 1 and 2 were identified as D-galactose, D-glucose and D-xylose in a ratio 1:4:1 and D-galactose and D-glucose in a ratio 1:4, respectively.

Reference： [1]Steroids,2012,vol. 77,p. 686 - 690

38
[ 87-72-9 ]
[ 2001-96-9 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 2414 - 2419
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 3002 - 3007
Zh. Obshch. Khim.,2016,vol. 25,p. 125 - 131,7

39
[ 87-72-9 ]
[ 107-35-7 ]
N-(D-lyxopyranosyl)taurine sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: Sodium methoxide (28 % in methanol, 2.23 g, 11.6 mmol) was added to <strong>[107-35-7]taurine</strong> (1.38 g, 11.0 mmol) in methanol (20 mL) and sonicated for a few minutes. To the resulting solution, D-glucose (1.80 g, 10.0 mmol) in methanol (20 mL) was added, sonicated for a few minutes, and stirred at 43 C for 24 h in an oil bath. After the reaction completion, absolute ethanol (approximately 40 mL) was added dropwise at 0 C with vigorous stirring until the precipitation stopped. The precipitate was filtered, washed with absolute ethanol, and dried in a vacuum desiccator. The reactions of other carbohydrates (D-galactose, D-xylose, D-arabinose, D-ribose, and D-lyxose) with <strong>[107-35-7]taurine</strong> were also carried out in the similar manner. The reaction conditions and purification methods are listed in Table 1.
	With sodium methylate; In methanol; at 20℃; for 23h;Inert atmosphere; Sonication;	Under argon 20 mL HPLC grade methanol in <strong>[107-35-7]taurine</strong> 1.3767g (11.00 mmol) of sodium methoxide and 2.2283g (28% in MeOH, 11.55 mmol) and the mixture was dissolved by ultrasonic treatment and then rigs source (lyxose) 1.5013g (10.00 mmol) of put dissolved by ultrasonic treatment.Then, the reaction was carried out for 23 hours with stirring at room temperature.After the reaction was over, stirring rapidly in an ice bath sikyeotgo generate a precipitate of absolute ethanol was added dropwise grade, was put further continued at least until the precipitate does not occur.If the precipitation is to occur, stop the dropping rapidly filtered salt of <strong>[107-35-7]taurine</strong> derivativeN- (Dand then obtaining a -lyxopyranosyl) <strong>[107-35-7]taurine</strong>, it was removed as residual impurities (methanol and ethanol), a vacuum pump.

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1863 - 1866
[2]Patent: KR2015/1340,2015,A .Location in patent: Paragraph 0157-0159

40
[ 87-72-9 ]
[ 107-35-7 ]
N-(β-D-xylopyranosyl)taurine sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: Sodium methoxide (28 % in methanol, 2.23 g, 11.6 mmol) was added to <strong>[107-35-7]taurine</strong> (1.38 g, 11.0 mmol) in methanol (20 mL) and sonicated for a few minutes. To the resulting solution, D-glucose (1.80 g, 10.0 mmol) in methanol (20 mL) was added, sonicated for a few minutes, and stirred at 43 C for 24 h in an oil bath. After the reaction completion, absolute ethanol (approximately 40 mL) was added dropwise at 0 C with vigorous stirring until the precipitation stopped. The precipitate was filtered, washed with absolute ethanol, and dried in a vacuum desiccator. The reactions of other carbohydrates (D-galactose, D-xylose, D-arabinose, D-ribose, and D-lyxose) with <strong>[107-35-7]taurine</strong> were also carried out in the similar manner. The reaction conditions and purification methods are listed in Table 1.

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 1863 - 1866

41
[ 87-72-9 ]
[ 98-01-1 ]
[ 591-11-7 ]
[ 22122-36-7 ]
[ 600-14-6 ]
[ 75-07-0 ]
[ 64-19-7 ]
[ 110-13-4 ]
[ 116-09-6 ]
[ 431-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	With alumina-doped tungstated mesoporous zirconia; In water; at 170℃;Inert atmosphere;	Batch catalytic experiments were performed under nitrogenatmosphere in tubular glass micro-reactors with pear-shaped bottomsand equipped with an appropriate PTFE-coated magneticstirring bar and a valve for gas purging. In a typical procedure, dxylose(30 mg), powdered catalyst (20 mg) and either water (1 mL,denoted W) or a solvent mixture (denoted W-T) comprising H2O(0.3 mL) and toluene (0.7 mL) were added to the reactor. The reactionmixtures were heated with a thermostatically controlled oilbath under magnetic stirring at 700 rpm, which was optimisedto avoid external mass transfer limitations; e.g. for ZrW(Cl), theinitial reaction rates (based on conversion at 30 min reaction)were similar for stirring rates at or above 700 rpm (9.4, 12.4 and12.1 mmol gcat-1 h-1 at 500, 700 and 900 rpm, respectively). Zerotime (considered as the instant the reaction began) was taken to bethe instant the micro-reactor was immersed in the oil bath. Aftera batch run, the catalyst was separated from the reaction mixtureby centrifugation, thoroughly washed with deionised water andfinally dried at 55 C overnight (giving the washed/dried solid) andcalcined at 450 C (1 C min-1) for 5 h (giving the recovered solid).The products present in the aqueous phase were analysed usinga Knauer K-1001 HPLC pump and a PL Hi-Plex H 300 mm × 7.7 mm(i.d.) ion exchange column (Polymer Laboratories Ltd., UK), coupledto a Knauer 2300 differential refractive index detector (for xylose)and a Knauer 2600 UV detector (280 nm, for Fur). The mobile phasewas 0.001 M H2SO4. The analytical conditions were the following:flow rate 0.6 mL min-1, column temperature 65 C. The Fur presentin the organic phase was quantified using a Gilson 306 HPLC pumpand a Spherisorb ODS S10 C18 column, coupled to a Gilson 118UV-vis detector (280 nm). The mobile phase consisted of 37% v/vmethanol and 63% v/v H2O (flow rate of 0.5 mL min-1). Authenticsamples of d-xylose and Fur were used as standards and calibrationcurves were used for quantification. The Fur yield (%) was calculatedusing the formula: [(moles of Fur formed)/(initial moles ofxylose)×100]. For each reaction time, at least two replicates ofan individual experiment were made; the reported results are theaverage values.

Reference： [1]Catalysis Today,2012,vol. 195,p. 127 - 135

42
[ 87-72-9 ]
[ 7341-96-0 ]
(E)-3-(β-D-xylopyranosyl)-acrylamide [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 5474 - 5477

43
[ 87-72-9 ]
[ 1570-05-4 ]
(2S,3R,4S,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayltetrakis(3,4-bis(benzyloxy)-5-bromobenzoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.8%		General procedure: The intermediate 3a-d (1.0 mmol) was dissolved in dichloromethane (10.0 mL), which has been dried through refluxing, under nitrogen atmosphere. Then, DMAP (1.5 mmol), EDCI (1.25mmol) were added to it in order. Then, ethylene glycol (0.5 mmol), glycerin (0.3 mmol), ribose (0.25 mmol) or xylose (0.25 mmol) was added. After stirring for 24 h at room temperature, the mixture was poured into water and washed with 1 mol/L HCl. The CH2Cl2 layer was concentrated, and the residue was purified using flash chromatography (ethyl acetate: Petroleum ether, 1:100-1:20) to obtain 4-6a, 4-7c or 4-7d. Compound 6-7a, 4-7b, 6d were used directly in the next step without purification and structural characterization.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 134,p. 24 - 33

44
3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→3)-O][(O-6-deoxy-α-L-mannopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-D-glucopyranosyloxy)-22-methoxyfurostane [ No CAS ]
[ 87-72-9 ]
[ 2280-44-6 ]
[ 10257-28-0 ]
[ 77-60-1 ]
[ 73-34-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4345 - 4349

45
[ 87-72-9 ]
[ 1103738-19-7 ]

Reference： [1]Patent: KR101770302,2017,B1

46
[ 87-72-9 ]
[ 1103738-17-5 ]

Reference： [1]Patent: KR101770302,2017,B1

47
[ 87-72-9 ]
[ 67-64-1 ]
[ 131156-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; copper(II) sulfate; at 20℃; for 24.0h;	Add D-xylose (15.0 g, 0.1 mol) to a 500 mL round bottom flaskAnhydrous copper sulfate (34.4 g, 0.216 mol) was added thereto, and 150 mL of acetone and 3 mL of 98% concentrated sulfuric acid were further added thereto, and the reaction was stirred at room temperature. The mixture is yellow-green and cloudy.When standing, the upper layer is a pale yellow liquid and the lower layer is a light blue solid.As the reaction proceeded, the turbid solution gradually turned tan. Reaction for 24 h,The resulting mixture was filtered under reduced pressure and the cake was light blue. The cake was washed with acetone and the filtrate was combined.A yellow transparent liquid is obtained. Concentrated aqueous ammonia was added dropwise to the filtrate to pH-7.0, and sulfuric acid was neutralized.A white floc precipitate (NH4)2S04 was formed. Filter (NH4) 2S04, filter cake washed with acetone,A colorless liquid is obtained. The filtrates were combined and dried in a single-necked flask using a rotary evaporator (temperature ? 50 C).Concentrated to a yellow brown syrupy substance.

Reference： [1]Patent: CN107722031,2018,A .Location in patent: Paragraph 0012

48
[ 87-72-9 ]
[ 100-61-8 ]
[ 93-90-3 ]