Name: 10016-20-3|α-Cyclodextrin|97%
Brand: Ambeed
SKU: A164223
Price: 5.0 USD
Availability: InStock
Rating: 90 (32 reviews)

1
[ 52-86-8 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₂₁H₂₃ClFNO₂ [ No CAS ]

Reference： [1]Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases,1985,vol. 81,p. 1247 - 1254

2
[ 18162-48-6 ]
[ 10016-20-3 ]
[ 90289-32-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	In pyridine; N,N-dimethyl-formamide at 100℃; for 18h;
86%	With pyridine; dmap In N,N-dimethyl-formamide at 100℃; for 18h;
75%	With pyridine; dmap In N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;

Reference： [1]Lai, Colin S. I.; Moody, Gwilym J.; Thomas, J. D. Ronald; Mulligan, David C.; Stoddart, J. Fraser; Zarzycki, Ryszard [Journal of the Chemical Society. Perkin transactions II, 1988, p. 319 - 324]
[2]Ashton; Boyd; Gattuso; Hartwell; Koniger; Spencer; Stoddart [Journal of Organic Chemistry, 1995, vol. 60, # 12, p. 3898 - 3903]
[3]Location in patent: experimental part Nagata, Takuya; Yoshikiyo, Keisuke; Matsui, Yoshihisa; Yamamoto, Tatsuyuki [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 2, p. 196 - 201]

3
[ 98-59-9 ]
[ 10016-20-3 ]
[ 32860-56-3 ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With pyridine at 20℃; Inert atmosphere;	1 Example 1: Synthesis of activated cyclodextrins Synthesis of mono-6-deoxy-6-(p-tolylsulfonyl)-a-cyclodextrin (a-CDOTs): p- Toluenesulfonyl chloride (634.0 mg, 2.96 mmol) was added to 50 ml pyridine solution of a- CD (5.0 g, mmol). After stirring overnight at room temperature in N2 atmosphere, the solution was evaporated and recrystallized in cold acetone from water. Alpha-CDOTs was obtained in a yield of 73.4%. The product were tracked by TLC (1-propanol: ethyl acetate: water: ΝΗ32Ο = 3:1 :2: 1 (v/v)) visualized with CAM solution.
26%	With pyridine for 0.25h;
20%

19.7%	With pyridine for 2h; Ambient temperature;
13.5%	Stage #1: alpha cyclodextrin With sodium hydroxide In water for 0.166667h; Stage #2: p-toluenesulfonyl chloride In water; acetonitrile at 20℃; for 2.33333h;	1.1 6^A-O-(p-Toluenesulfonyl)α-CD (2) α-CD (10.0g, 10.3 mmol) was suspended in 20 mL of water, and NaOH (1.23 g, 30.7 mmol) in 3.0 mL of water was added dropwise over 10 min. The suspension became homogeneous after the addition was complete. p-Toluenesulfonyl chloride (1.96 g, 10.3 mmol) in 4.0 mL CH3CN was added dropwise over 20 min. A white precipitate was visible immediately after the start of the addition. The reaction mixture was stirred another 2 h at room temperature and then filtered. The filtrate was acidified to about pH 7-8 with 1N HCl and the product allowed to precipitate at 4 C° overnight. The resulting white precipitate was recovered by suction filtration to provide 3.49 g of crude product. Recrystalize the solid using hot water and dried at 60 °C for 24 h under vacuum to afford 2 (1.57 g) as a white solid in 13.5% yield. Rf = 0.55 (n-BuOH/C2H5OH/H2O = 5:4:3). 1H NMR (400 MHz, D2O): δ 7.98 (d, 2H, J = 8.1 Hz), 7.56 (d, 2H, J = 8.1 Hz), 5.05 - 5.06 (m, 5H), 4.90 (d, 1H, J = 3.0 Hz), 4.42 (dd, 1H, J = 3.0, 10.0 Hz), 4.10 (t, 1H, J = 9.1 Hz), 3.47 - 3.89 (m, 34H); 13C NMR (100 MHz, CDCl3): δ 146.30, 131.60, 130.28, 128.30, 101.80, 101.55, 101.44, 101.33, 98.50, 81.48, 81.37, 81.28, 81.21, 81.14, 78.92, 73.49, 73.41, 73.26, 72.58, 72.20, 72.12, 72.01, 71.95, 71.89, 71.76, 71.64, 71.45, 71.28, 70.06, 60.49, 60.34, 60.24, 60.12, 21.32.
10%	With pyridine at 20℃; for 0.25h;	4 [31 ,32,33,34,35,36,37,38,39,40,41,42-Dodecahy- droxy-1 0,1 5,20,25,30-pentakis(hydroxymethyl)-2,4, 7,9,12,14,17,1 9,22,24,27,29-dodecaoxaheptacycloyl]methyl 4-methyl benzene-1-sulfonate (14)2 To a solution of a-cyclodextrin (13, lOg, lOmmol) in dry pyridine (Py) (0.32 L) was added 4-toluenesulfonyl chloride (TsC1) (20 g, 0.10 mol) at room temperature. The mixture was stirred at this temperature for 15 minutes and was quenched with water (60 mE) immediately. The reaction mixture was concentrated under reduce pressure to remove the volatiles (pyridine and water). The residue was purified by reversed phase flash chromatography (0-25% of acetonitrile in water) to give product 14 (1.1 g, 10% yield) as a white solid. ESI mlz: 1127 (M+H).
	With pyridine for 5h; Ambient temperature;
2.1 g	With pyridine for 5h; Ambient temperature;
	With pyridine
	With pyridine at 20℃;
	With pyridine at 20℃;
	With pyridine regioselective reaction;
	In water at 25℃;
	With pyridine
	With pyridine at 20℃; for 0.0833333h;

Reference： [1]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - WO2016/126910, 2016, A1 Location in patent: Page/Page column 29
[2]Location in patent: experimental part Chwalek, Martin; Auzely, Rachel; Fort, Sebastien [Organic and Biomolecular Chemistry, 2009, vol. 7, # 8, p. 1680 - 1688]
[3]Casati, Costanza; Franchi, Paola; Pievo, Roberta; Mezzina, Elisabetta; Lucarini, Marco [Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19108 - 19117]
[4]Brown, Susan E.; Coates, John H.; Coghlan, Daniel R.; Easton, Christopher J.; Eyk, Stephen J. van; et al. [Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 953 - 958]
[5]Xiao, Sulong; Wang, Qi; Si, Longlong; Zhou, Xiaoshu; Zhang, Yongmin; Zhang, Lihe; Zhou, Demin [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1 - 9]
[6]Current Patent Assignee: REGENERON PHARMACEUTICALS INC - US2018/333504, 2018, A1 Location in patent: Paragraph 0364
[7]Takahashi, Keiko; Hattori, Kenjiro; Toda, Fujio [Tetrahedron Letters, 1984, vol. 25, # 31, p. 3331 - 3334]
[8]Hamasaki, Keita; Ikeda, Hiroshi; Nakamura, Asao; Ueno, Akihiko; Toda, Fujio; Suzuki, Iwao; Osa, Tetsuo [Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5035 - 5040]
[9]Uekama; Minami; Hirayama [Journal of medicinal chemistry, 1997, vol. 40, # 17, p. 2755 - 2761]
[10]Banerjee, Ipsita A.; Yu, Lingtao; Matsui, Hiroshi [Journal of the American Chemical Society, 2003, vol. 125, # 32, p. 9542 - 9543]
[11]Hoshino; Miyauchi; Kawaguchi; Yamaguchi; Harada [Journal of the American Chemical Society, 2000, vol. 122, # 40, p. 9876 - 9877]
[12]Location in patent: scheme or table Hein, Christopher D.; Liu, Xin-Ming; Chen, Fu; Cullen, Diane M.; Wang, Dong [Macromolecular Bioscience, 2010, vol. 10, # 12, p. 1544 - 1556]
[13]Popr, Martin; Hybelbauerova, Simona; Jindrich, Jindrich [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1390 - 1396]
[14]Guo, Kun; Zhang, Da-Li; Zhang, Xiao-Mei; Zhang, Jian; Ding, Li-Sheng; Li, Bang-Jing; Zhang, Sheng [Angewandte Chemie - International Edition, 2015, vol. 54, # 41, p. 12127 - 12133][Angew. Chem., 2015, vol. 127, p. 12295 - 12301,7]
[15]Zhang, Qi-Wei; Elemans, Johannes A. A. W.; White, Paul B.; Nolte, Roeland J. M. [Chemical Communications, 2018, vol. 54, # 44, p. 5586 - 5589]
[16]Current Patent Assignee: REGENERON PHARMACEUTICALS INC - WO2019/217591, 2019, A1 Location in patent: Paragraph 0545

4
[ 10016-20-3 ]
[ 50-81-7 ]
[ 129499-78-1 ]

Reference： [1]Agricultural and Biological Chemistry,1991,vol. 55,p. 1751 - 1756
[2]ACS Catalysis,2016,vol. 6,p. 1606 - 1615

5
[ 10016-20-3 ]
[ 131105-41-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 70℃; for 20h; Inert atmosphere;	11 Example 11; Compound 7 To a solution of triphenylphosphine (16.3 g, 62.1 mmol) and iodine (16.8 g, 66.24 mmol) in dry DMF (80 mL) was added CD (5 g, 4.14 mmol) and the solution was stirred at 70°C during 20 h. It was then concentrated under reduced pressure to about 30 mL and the pH was adjusted to 9 by addition of sodium methoxide in methanol (3M, 30 mL). The solution was kept at room temperature for 30 min, after what it was poured into ice water (20mL/mmol). The precipitate was collected by filtration and washed with methanol to afford 6-deoxy-6- iodo-CDs 6 in a quantitative yield.
91%	With tetraethylammonium iodide; 4-pyrrolidin-1-ylpyridine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In N,N-dimethyl-formamide at 20℃; regioselective reaction;	Per(6-deoxy-6-halo)cyclodextrins 2; General Procedure General procedure: To a solution of freshly dried cyclodextrin 1 (2 mmol) in anhydrous DMF (40 mL) were added XtalFluor-E (2 equiv per glucose unit),4-(1-pyrrolidino)pyridine (1 equiv per glucose unit) and an anhydrous tetraethylammonium halide (2 equiv per glucose unit) with stirring at r.t. After the reaction was complete, as monitored by TLC, DMF was removed under reduced pressure and the resulting residue was poured into sat. Na2CO3 solution (50 mL); the reaction mixture was stirred for another 1 h. Addition of cold acetone (200mL) gave a precipitate which was collected by filtration and exhaustively washed with H2O and acetone to afford 2 as a white or pale brown solid.
80%	With Iod; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 15h;

80.2%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 18h;
80%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 70℃; for 19h; Inert atmosphere;	1.1 (1) Weigh 12.12g of triphenylphosphine and add it to 50mL of DMF, then slowly add 12.27g of iodine under stirring, stir for 0.25h, and then add 3.0g of dry α-cyclodextrin, N2 Protect, stir at 70°C for 19h; after the reaction is finished, spin off 2/3 volume of DMF, then add 3mol/L sodium methoxide methanol solution to quench,Precipitating with acetone and drying to obtain 4g of (6-I)α-cyclodextrin with a yield of 80%;
75%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 20℃;
71%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
66%	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	5.1 Synthesis of hexakis (6-deoxy-6-iodo)-α-CD (2) To a solution of triphenylphosphane (10.38 g/39.6 mmol) and iodine (10.06 g/39.6 mmol) in dry DMF (50 mL) was added α-CD (6 mmol) and the solution was stirred at 80oC overnight. It was then concentrated using a rotary evaporator vacuum (EYELA N-1100DWD, Tokyo Rikakikai, Tokyo, Japan) to about 20 mL and the pH adjusted to 9 by addition of sodium methoxide in methanol (3M). The solution was kept at room temperature for 30 min to destroy the formate esters formed in the reaction, after which it was poured into ice water. The precipitate was collected by filtration and washed with methanol to yield 6-deoxy-6-iodo-α-CD 2. Yield 66%; 1H NMR (400 MHz, DMSO-d6): δ 5.59 (br s, 12H), 4.86-4.93 (m, 6H), 3.79 (br s, 6H), 3.70 (br s, 6H), 3.59 (br s, 6H), 3.50 (d, 6H, J = 7.2 Hz), 3.32 (br s, 12H, overlap with H2O); 13C NMR (100 MHz, DMSO-d6): δ 101.79, 86.29, 72.20, 71.69, 70.63, 9.69; HRMS Calcd for C36H54I6NaO24 [M+Na]+: 1654.7166. Found 1654.7132.
	With methanol; iodine; sodium methylate; triphenylphosphine 1.) DMF, 80 deg C, 18h, 2.) pH 9-10, r.t., 30 min; Yield given. Multistep reaction;
	With iodine; triphenylphosphine
	With iodine; triphenylphosphine In N,N-dimethyl-formamide at 80℃;
	With iodine; triphenylphosphine In N,N-dimethyl-formamide
	With iodine; triphenylphosphine In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; NANTES UNIVERSITE - WO2018/149945, 2018, A1 Location in patent: Page/Page column 54; 55
[2]Liu, Xiaofeng; Cheng, Sen; Wang, Xiaolei; Xue, Weihua [Synthesis, 2013, vol. 45, # 22, p. 3103 - 3105]
[3]Gadelle, Andree; Defaye, Jacques [Angewandte Chemie, 1991, vol. 103, # 1, p. 94 - 95]
[4]Kraus, Tomas; Budesinsky, Milos; Zavada, Jiri [Collection of Czechoslovak Chemical Communications, 1998, vol. 63, # 4, p. 534 - 540]
[5]Current Patent Assignee: KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN112266327, 2021, A Location in patent: Paragraph 0027-0028
[6]Chen, Yingying; Si, Longlong; Wang, Xinchen; Xiao, Sulong; Zhang, Bo; Zhang, Lihe; Zhang, Yongmin; Zhou, Demin; Zhu, Yinbiao [Molecular Pharmaceutics, 2020, vol. 17, # 7, p. 2546 - 2554]
[7]Alali, Urjwan; Vallin, Aurélie; Bil, Abed; Khanchouche, Takwa; Mathiron, David; Przybylski, Cédric; Beaulieu, Rémi; Kovensky, José; Benazza, Mohammed; Bonnet, Véronique [Organic and Biomolecular Chemistry, 2019, vol. 17, # 30, p. 7228 - 7237]
[8]Tian, Zhenyu; Meng, Kun; Shi, Yanhong; Zhang, Naixia; Liu, Xuehui; Jin, Hongwei; Zhang, Yongmin; Zhang, Lihe; Zhou, Demin; Xiao, Sulong [Tetrahedron, 2017, vol. 73, # 17, p. 2512 - 2517]
[9]Baer; Vargas Berenguel; Shu; Defaye; Gadelle; Santoyo Gonzalez [Carbohydrate Research, 1992, vol. 228, # 1, p. 307 - 314]
[10]Prudden, Anthony R.; Lien, Nathan R.; Telford, Jason R. [Chemical Communications, 2004, # 2, p. 172 - 173]
[11]Tian, Zhenyu; Si, Longlong; Meng, Kun; Zhou, Xiaoshu; Zhang, Yongmin; Zhou, Demin; Xiao, Sulong [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 133 - 139]
[12]Chen, Lei; Chen, Yong; Zhang, Yi; Liu, Yu [Angewandte Chemie - International Edition, 2021, vol. 60, # 14, p. 7654 - 7658][Angew. Chem., 2021, vol. 133, # 14, p. 7732 - 7736,5]
[13]Chen, Yingying; Gao, Qianqian; Liang, Shuobin; Ma, Xinyuan; Tretyakova, Elena V.; Wang, Xinchen; Xiao, Sulong; Zhang, Yongmin; Zhou, Demin [Molecules, 2022, vol. 27, # 4]

6
[ 10016-20-3 ]
[ 53784-82-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrabutylammomium bromide; (chloro-phenylthio-methylene)dimethylammonium chloride In N,N-dimethyl-formamide at 20℃; regioselective reaction;
95%	With tetraethylammonium bromide; 4-pyrrolidin-1-ylpyridine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In N,N-dimethyl-formamide at 20℃; regioselective reaction;	Per(6-deoxy-6-halo)cyclodextrins 2; General Procedure General procedure: To a solution of freshly dried cyclodextrin 1 (2 mmol) in anhydrous DMF (40 mL) were added XtalFluor-E (2 equiv per glucose unit),4-(1-pyrrolidino)pyridine (1 equiv per glucose unit) and an anhydrous tetraethylammonium halide (2 equiv per glucose unit) with stirring at r.t. After the reaction was complete, as monitored by TLC, DMF was removed under reduced pressure and the resulting residue was poured into sat. Na2CO3 solution (50 mL); the reaction mixture was stirred for another 1 h. Addition of cold acetone (200mL) gave a precipitate which was collected by filtration and exhaustively washed with H2O and acetone to afford 2 as a white or pale brown solid.
86%	With bromine; triphenylphosphine In N,N-dimethyl-formamide at 75 - 80℃; for 18h;

85%	With bromine; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 17h;
76%	With bromine; triphenylphosphine In N,N-dimethyl-formamide at 70℃;
	With methanol; bromine; sodium methylate; triphenylphosphine 1.) DMF, 80 deg C, 15 h, 2.) pH 9-10, r.t., 30 min; Yield given. Multistep reaction;
	With N-(bromomethylene)-N-methylmethanaminium bromide In N,N-dimethyl-formamide at 80℃; for 18h; Yield given;
	With bromomethylenemorpholinium bromide; sodium methylate 1.) DMF, 45 deg C, 2.) methanol; Yield given. Multistep reaction;
	With bromine; triphenylphosphine In N,N-dimethyl-formamide at 75 - 80℃;
	With N-Bromosuccinimide; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 4h;
	With N-Bromosuccinimide; triphenylphosphine In N,N-dimethyl-formamide
	Stage #1: alpha cyclodextrin With N-(bromomethylene)-N-methylmethanaminium bromide In N,N-dimethyl-formamide at 70℃; for 4h; Stage #2: With water at 40℃; for 6h;
372 mg	With N-Bromosuccinimide; triphenylphosphine In N,N-dimethyl-formamide at 90℃;

Reference： [1]Location in patent: experimental part Xue, Weihua; Zhang, Lifen [Synthesis, 2011, # 22, p. 3612 - 3614]
[2]Liu, Xiaofeng; Cheng, Sen; Wang, Xiaolei; Xue, Weihua [Synthesis, 2013, vol. 45, # 22, p. 3103 - 3105]
[3]Mourtzis, Nikolaos; Eliadou, Kyriaki; Aggelidou, Chrysie; Sophianopoulou, Vassiliki; Mavridis, Irene M.; Yannakopoulou, Konstantina [Organic and Biomolecular Chemistry, 2007, vol. 5, # 1, p. 125 - 131]
[4]Chmurski, Kazimierz; Coleman, Antony W.; Jurczak, Janusz [Journal of Carbohydrate Chemistry, 1996, vol. 15, # 7, p. 787 - 796]
[5]Location in patent: scheme or table Maffeo, Davide; Lampropoulou, Maria; Fardis, Michael; Lazarou, Yannis G.; Mavridis, Irene M.; Mavridou, Despoina A. I.; Urso, Elena; Pratsinis, Harris; Kletsas, Dimitris; Yannakopoulou, Konstantina [Organic and Biomolecular Chemistry, 2010, vol. 8, # 8, p. 1910 - 1921]
[6]Baer; Vargas Berenguel; Shu; Defaye; Gadelle; Santoyo Gonzalez [Carbohydrate Research, 1992, vol. 228, # 1, p. 307 - 314]
[7]Gorin, Boris I.; Riopelle, Richard J.; Thatcher, Gregory R. J. [Tetrahedron Letters, 1996, vol. 37, # 27, p. 4647 - 4650]
[8]Chmurski, Kazimierz; Defaye, Jacques [Tetrahedron Letters, 1997, vol. 38, # 42, p. 7365 - 7368]
[9]Vizitiu, Dragos; Walkinshaw, Caroline S.; Gorin, Borio I.; Thatcher, Gregory R. J. [Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8760 - 8766]
[10]Falvey, Patrick; Lim, Choon Woo; Darcy, Raphael; Revermann, Tobias; Karst, Uwe; Giesbers, Marcel; Marcelis, Antonius T. M.; Lazar, Adina; Coleman, Anthony W.; Reinhoudt, David N.; Ravoo, Bart Jan [Chemistry - A European Journal, 2005, vol. 11, # 4, p. 1171 - 1180]
[11]Location in patent: scheme or table Seyedi, Seyed Mohammad; Sadeghian, Hamid; Jabbari, Atena; Assadieskandar, Amir; Momeni, Hamideh [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 14, p. 4307 - 4311]
[12]Zultanski, Susan L.; Kuhl, Nadine; Zhong, Wendy; Cohen, Ryan D.; Reibarkh, Mikhail; Jurica, Jon; Kim, Jungchul; Weisel, Lauren; Ekkati, Anil R.; Klapars, Artis; Gauthier, Donald R.; McCabe Dunn, Jamie M. [Organic Process Research and Development, 2021, vol. 25, # 3, p. 597 - 607]
[13]Cherraben, Sawsen; Scelle, Jérémy; Hasenknopf, Bernold; Vives, Guillaume; Sollogoub, Matthieu [Organic Letters, 2021, vol. 23, # 20, p. 7938 - 7942]

7
[ 2106-10-7 ]
[ 7585-39-9 ]
[ 10016-20-3 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 5605 - 5608

8
[ 26549-24-6 ]
[ 10016-20-3 ]
α-cyclodextrin * (R)-(-)-2-hexanol [ No CAS ]

Reference： [1]Journal of Physical Chemistry,1994,vol. 98,p. 10282 - 10288

9
[ 18162-48-6 ]
[ 10016-20-3 ]
[ 118646-79-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine at 0 - 20℃;
80%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h;
77.2%	With pyridine at 20℃; for 12h;

76%	With pyridine at 20℃; for 24h;	Synthesis of 3 To a solution of α-CD (3.00 g, 3.08 mmol) in dry pyridine (20 ml) was added a solution of ClSiMe2(t-Bu) (8.36 g, 55.4 mmol) in dry pyridine (20 ml) at r.t.. The mixture was allowed to stir at r.t. for 24 h. The resulted precipitates were collected by filtration and then dissolved with ethyl acetate.The organic solution was washed with HCl aq twice and then with water. The organic layer was separated and dried over anhydrous sodium sulfate. Removal of solvent gave 3a (3.88 g, 76 % yield) as white powder. The corresponding 3b was synthesized by the same procedure using β-CD instead of α-CD.
75%	With 1H-imidazole In N,N-dimethyl-formamide
75%	With pyridine at 0 - 20℃;
69%	With pyridine for 24h; Ambient temperature;
50%	With pyridine Ambient temperature;
50%	In pyridine
	With pyridine
	With pyridine; 1H-imidazole at 20℃; for 8h;
	With pyridine for 24h;

Reference： [1]Meppen, Malte; Wang, Yonghui; Cheon, Hwan-Sung; Kishi, Yoshito [Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 1941 - 1950]
[2]Anderson, Harry L.; Caycedo-Soler, Felipe; Frawley, Andrew T.; Huelga, Susana F.; Kendrick, William J.; Mattioni, Andrea; Plenio, Martin B.; Pruchyathamkorn, Jiratheep [Angewandte Chemie - International Edition, 2020, vol. 59, # 38, p. 16455 - 16458][Angew. Chem., 2020, vol. 132, # 38, p. 16597 - 16600,4]
[3]Sukegawa, Takeshi; Furuike, Tetsuya; Niikura, Kenichi; Yamagishi, Akihiko; Monde, Kenji; Nishimura, Shin-Ichiro [Chemical Communications, 2002, # 5, p. 430 - 431]
[4]Karube, Nobuyuki; Ito, Kazuaki [Letters in Organic Chemistry, 2014, vol. 11, # 10, p. 719 - 724]
[5]Immel, Stefan; Lichtenthaler, Frieder W.; Lindner, Hans J.; Fujita, Kahee; Fukudome, Makato; Nogami, Yasuyoshi [Tetrahedron Asymmetry, 2000, vol. 11, # 1, p. 27 - 36]
[6]Location in patent: experimental part Grachev; Edunov; Kurochkina; Levina; Nifant'ev [Russian Journal of General Chemistry, 2011, vol. 81, # 2, p. 322 - 329]
[7]Venema, Fokke; Nelissen, Hubertus F. M.; Berthault, Patrick; Birlirakis, Nicolaos; Rowan, Alan E.; Feiters, Martinus C.; Nolte, Roeland J. M. [Chemistry - A European Journal, 1998, vol. 4, # 11, p. 2237 - 2250]
[8]Jullien, Ludovic; Canceill, Josette; Lacombe, Liliane; Lehn, Jean-Marie [Journal of the Chemical Society. Perkin transactions II, 1994, # 5, p. 989 - 1002]
[9]Grachev [Russian Journal of General Chemistry, 1999, vol. 69, # 11, p. 1702 - 1707]
[10]Wazynska, Monika; Temeriusz, Andrzej; Chmurski, Kazimierz; Bilewicz, Renata; Jurczak, Janusz [Tetrahedron Letters, 2000, vol. 41, # 47, p. 9119 - 9123]
[11]Dubes, Alix; Degobert, Ghania; Fessi, Hatem; Parrot-Lopez, Helene [Carbohydrate Research, 2003, vol. 338, # 21, p. 2185 - 2193]
[12]Location in patent: scheme or table Aime, Silvio; Gianolio, Eliana; Arena, Francesca; Barge, Alessandro; Martina, Katia; Heropoulos, George; Cravotto, Giancarlo [Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 370 - 379] Location in patent: scheme or table Cravotto, Giancarlo; Mendicuti, Francisco; Martina, Katia; Tagliapietra, Silvia; Robaldo, Bruna; Barge, Alessandro [Synlett, 2008, # 17, p. 2642 - 2646]
[13]McKee, James A.; Green, Thomas K. [Tetrahedron Letters, 2015, vol. 56, # 30, p. 4451 - 4454]

10
[ 10016-20-3 ]
[ 33057-59-9 ]
6^I,6^IV-dideoxy-6^I,6^IV-diazido-α-cyclodextrin [ No CAS ]
C₃₆H₅₈N₆O₂₈ [ No CAS ]
6^A,6^B-diazido-6^A,6^B-dideoxy-α-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With lithium azide; carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide for 6h; Ambient temperature; Further byproducts given. Yields of byproduct given;
18%	With lithium azide; carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide for 6h; Ambient temperature; Yield given. Further byproducts given;
18%	With lithium azide; carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide for 6h; Ambient temperature; Further byproducts given. Title compound not separated from byproducts;

3.69 g

Stage #1: alpha cyclodextrin With N-Bromosuccinimide; triphenylphosphine In N,N-dimethyl-formamide at 8 - 50℃; for 7.5h; Inert atmosphere; Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; for 5h;

Synthesis of 6A,6X-diazido-α-CDs via dibromo-α-CD intermediates6A,6X-Diazido-6A,6X-dideoxy-α-cyclodextrin (4, reaction 3): 6A,6X-Brominated α-CD 5 was prepared according to the modified procedure [3].Triphenylphosphine (36.4 g, 138 mmol) was dissolved in 125 mL of freshly distilledDMF under Ar atmosphere. The solution was cooled down to 8 °C, and NBS wasslowly added to the solution which became dark violet. Dried α-CD (1, 25 g, 25.7mmol) was dissolved in 100 mL of DMF and added in one portion during 20 minutesto the dark violet reaction mixture. The mixture was heated up to 50 °C, and theconversion to dibromo-α-CD was monitored by direct phase TLC (eluent B). After 7.5h the reaction was stopped by addition of 100 mL of MeOH. After 10 minutes ofvigorous stirring, the red-violet reaction mixture was cooled and poured to 1.3 mL ofMeOH (pH 3). Addition of sodium methoxide solution (100 mL) resulted in slowprecipitation (pH 12). The yellowish precipitate was recovered by filtration, washed with MeOH (3 × 300 mL) and dried to constant weight in a vacuum drying box in thepresence of P2O5 and KOH. The white solid (15.27 g), containing unreacted α-CD (1, ≈ 35% based on TLC, Rf =0.15, eluent B), monobromo-α-CD (≈ 35% based on TLC, Rf = 0.25, eluent B),dibromo-α-CD (5, ≈ 20% based on TLC, Rf = 0.35, eluent B) and oversubstitutedproducts (less than 10% based on TLC, Rf = 0.5, eluent B) was dissolved in DMF(300 mL), sodium azide (2.72 g, 42.0 mmol) was added, and the mixture was heatedto 80 °C for 5 h. DMF was removed under reduced pressure at 60 °C and theyellowish residue was poured into acetone (1.3 L) under vigorous stirring. The whiteprecipitate was recovered by filtration, washed with acetone (3 × 100 mL) and driedto constant weight (17.9 g) in a vacuum drying box in the presence of P2O5 and KOH.Direct-phase TLC (eluent B) and reversed-phase HPLC (ACN/H2O gradient elution)analysis revealed that the precipitate contained unreacted α-CD (1, Rf = 0.15),monoazido-α-CD (7, Rf = 0.35) and diazido-α-CD (4, Rf = 0.45). The diazido-α-CDfraction was isolated by direct column chromatography. One-third of the precipitatewas dissolved in ACN/water/NH3 (25%) 10:7:1 (40 mL) and injected to thechromatographic column (310 g). After chromatographic separation of all threeportions of the crude mixture using mobile phase ACN/water/NH3 (25%) 10:5:1, the6A,6X-diazido-α-CD 4 (1.26 g, 5% yield) was obtained as a white solid material. 6A-Azido-α-CD 7 was also obtained as a white solid (3.69 g, 15% yield) as the secondeluted compound.

Reference： [1]Hanessian; Benalil; Laferriere [Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4786 - 4797]
[2]Hanessian; Benalil; Laferriere [Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4786 - 4797]
[3]Hanessian; Benalil; Laferriere [Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4786 - 4797]
[4]Tichá, Iveta; Benkovics, Gábor; Malanga, Milo; Jindřich, Jindřich [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2829 - 2837]

11
[ 10016-20-3 ]
[ 173094-59-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetraethylammonium chloride; 4-pyrrolidin-1-ylpyridine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In N,N-dimethyl-formamide at 20℃; regioselective reaction;	Per(6-deoxy-6-halo)cyclodextrins 2; General Procedure General procedure: To a solution of freshly dried cyclodextrin 1 (2 mmol) in anhydrous DMF (40 mL) were added XtalFluor-E (2 equiv per glucose unit),4-(1-pyrrolidino)pyridine (1 equiv per glucose unit) and an anhydrous tetraethylammonium halide (2 equiv per glucose unit) with stirring at r.t. After the reaction was complete, as monitored by TLC, DMF was removed under reduced pressure and the resulting residue was poured into sat. Na2CO3 solution (50 mL); the reaction mixture was stirred for another 1 h. Addition of cold acetone (200mL) gave a precipitate which was collected by filtration and exhaustively washed with H2O and acetone to afford 2 as a white or pale brown solid.
90%	With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃; for 48h;
80%	With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃; for 48h;

	With chloromethylenemorpholinium chloride; sodium methylate 1.) DMF, 60 deg C, 20 h, 2.) methanol; Yield given. Multistep reaction;
	With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃; for 48h;
	With methanesulfonyl chloride In N,N-dimethyl-formamide at 75℃; for 4.5h; Inert atmosphere;
	With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃;
	Stage #1: alpha cyclodextrin With Vilsmeier reagent In N,N-dimethyl-formamide at 70℃; for 4h; Stage #2: With water at 40℃; for 6h;

Reference： [1]Liu, Xiaofeng; Cheng, Sen; Wang, Xiaolei; Xue, Weihua [Synthesis, 2013, vol. 45, # 22, p. 3103 - 3105]
[2]Guillo, Frederique; Hamelin, Bertrand; Jullien, Ludovic; Canceill, Josette; Lehn, Jean-Marie; et al. [Bulletin de la Societe Chimique de France, 1995, vol. 132, # 8, p. 857 - 866]
[3]Möller, Nadja; Hellwig, Tim; Stricker, Lucas; Engel, Sabrina; Fallnich, Carsten; Ravoo, Bart Jan [Chemical Communications, 2017, vol. 53, # 1, p. 240 - 243]
[4]Chmurski, Kazimierz; Defaye, Jacques [Tetrahedron Letters, 1997, vol. 38, # 42, p. 7365 - 7368]
[5]Falvey, Patrick; Lim, Choon Woo; Darcy, Raphael; Revermann, Tobias; Karst, Uwe; Giesbers, Marcel; Marcelis, Antonius T. M.; Lazar, Adina; Coleman, Anthony W.; Reinhoudt, David N.; Ravoo, Bart Jan [Chemistry - A European Journal, 2005, vol. 11, # 4, p. 1171 - 1180]
[6]Okamatsu, Ayaka; Motoyama, Keiichi; Onodera, Risako; Higashi, Taishi; Koshigoe, Takahiro; Shimada, Yasutaka; Hattori, Kenjiro; Takeuchi, Tomoko; Arima, Hidetoshi [Biomacromolecules, 2013, vol. 14, # 12, p. 4420 - 4428]
[7]Le, Hoa Thi; Park, Seung Cheol; Kang, Chulhun; Lim, Choon Woo; Kim, Tae Woo [Organic and Biomolecular Chemistry, 2015, vol. 13, # 30, p. 8291 - 8297]
[8]Zultanski, Susan L.; Kuhl, Nadine; Zhong, Wendy; Cohen, Ryan D.; Reibarkh, Mikhail; Jurica, Jon; Kim, Jungchul; Weisel, Lauren; Ekkati, Anil R.; Klapars, Artis; Gauthier, Donald R.; McCabe Dunn, Jamie M. [Organic Process Research and Development, 2021, vol. 25, # 3, p. 597 - 607]

12
[ 538-41-0 ]
[ 135-51-3 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₃₂H₁₈N₆O₁₄S₄^(4-)*4Na⁽¹⁺⁾ [ No CAS ]
C₃₂H₁₈N₆O₁₄S₄^(4-)*4Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 1310 - 1313

13
[ 10016-20-3 ]
[ 33057-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium azide; carbon tetrabromide; triphenylphosphine 1.) DMF, room temperature, 24 h; Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: pyridine 2: sodium azide / H₂O
	Multi-step reaction with 2 steps 1: 2.1 g / pyridine / 5 h / Ambient temperature 2: 3.08 g / sodium azide / H₂O / 5 h / 80 °C

	Multi-step reaction with 2 steps 2: sodium azide / N,N-dimethyl-formamide / 140 °C
	Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 0.17 h 1.2: 2.33 h / 20 °C 2.1: sodium azide / water / 12 h / 80 °C
	Multi-step reaction with 2 steps 1: pyridine / 0.08 h / 20 °C 2: sodium azide / water / 16 h / 80 °C
18.4 mg	Stage #1: alpha cyclodextrin With pyridine; p-toluenesulfonyl chloride at 0 - 20℃; for 23h; Molecular sieve; Stage #2: With sodium azide In N,N-dimethyl-formamide at 90℃; for 22h;	6-NH₂-a-CD -1V209 (8) To a suspension of a-cyclodextrin (360 mg, 0.370 mmol) and MS3A in anhydrous pyridine (35 mL) was added dropwise a solution of p-toluenesulfonyl chloride (64.3 mg, 0.34 mmol) in anhydrous pyridine (6 mL) at 0 °C. The mixture was stirred and warmed to room temperature. After stirring for 23 h, the mixture was filtered through Celite pad, concentrated in vacuo, and azeotroped with toluene. Obtained white solid was then dissolved in DMF (10 mL) and NaN3 (34.5 mg, 0.531 mmol) was added, and the mixture was stirred at 90 °C for 22 h. After concentration of the reaction mixture, the residue was purified by ODS column chromatography (H2O/methanol) to give mono azido a-CD as a white solid (18.4 mg, 5%, 2 steps). HRMS (positive mode) Found: m/z 1020.3126 [(M+Na)+], calculated for C36H59N3NaO29: 1020.3126. To a solution of mono azido a-CD (16.7 mg, 16.8 mmol) in H2O (3 mL) was added 10% Pd/C (16.9 mg). The reaction mixture was stirred at room temperature for 16 h under H2 atmosphere. After removal of insoluble materials by membrane filtration, the filtrate was concentrated in vacuo. Obtained mono amino a-CD was then dissolved in DMF/H2O (1:1, 1 mL) and a solution of 1V209 (6.40 mg, 17.8 mmol) in anhydrous DMF (0.5 mL), HATU (16.5 mg, 43.4 mmol), and TEA (5 μL, 35.9 mmol) were added. The mixture was stirred at room temperature for 26 h. The reaction was quenched by addition of H2O and the mixture was concentrated in vacuo. The residue was purified by ODS column chromatography (H2O/methanol) and preparative HPLC (eluent; 40% methanol in H2O) to give compound 8 as a white solid (6.0 mg, 27%).

Reference： [1]Jimenez Blanco, Jose Luis; Garcia Fernandez, Jose Manuel; Gadelle, Andree; Defaye, Jacques [Carbohydrate Research, 1997, vol. 303, # 3, p. 367 - 372]
[2]Uekama; Minami; Hirayama [Journal of medicinal chemistry, 1997, vol. 40, # 17, p. 2755 - 2761]
[3]Hamasaki, Keita; Ikeda, Hiroshi; Nakamura, Asao; Ueno, Akihiko; Toda, Fujio; Suzuki, Iwao; Osa, Tetsuo [Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5035 - 5040]
[4]Casati, Costanza; Franchi, Paola; Pievo, Roberta; Mezzina, Elisabetta; Lucarini, Marco [Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19108 - 19117]
[5]Xiao, Sulong; Wang, Qi; Si, Longlong; Zhou, Xiaoshu; Zhang, Yongmin; Zhang, Lihe; Zhou, Demin [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1 - 9]
[6]Current Patent Assignee: REGENERON PHARMACEUTICALS INC - WO2019/217591, 2019, A1
[7]Baba, Akihito; Wakao, Masahiro; Shinchi, Hiroyuki; Chan, Michael; Hayashi, Tomoko; Yao, Shiyin; Cottam, Howard B.; Carson, Dennis A.; Suda, Yasuo [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 3]

14
[ 2232-08-8 ]
[ 10016-20-3 ]
[ 56503-24-3 ]
[ 93184-10-2 ]

Reference： [1]Journal of Carbohydrate Chemistry,1998,vol. 17,p. 489 - 494

15
[ 13435-12-6 ]
[ 10016-20-3 ]
hexakis(2,6-di-O-trimethylsilyl)cyclomaltohexaose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In N,N-dimethyl-formamide at 50℃; for 48h;

Reference： [1]Bukowska, Maria; MacIejewski, Mieczyslaw; Prejzner, Jan [Carbohydrate Research, 1998, vol. 308, # 3-4, p. 275 - 279]

16
[ 10016-20-3 ]
[ 17557-23-2 ]
2C₃₆H₆₀O₃₀*C₁₁H₂₀O₄ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 1541 - 1545

22
[ 108-24-7 ]
[ 10016-20-3 ]
[ 23661-37-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	In pyridine
100%	With iodine at 20℃; for 24h; neat (no solvent);
100%	With pyridine at 60℃; for 12h;

100%	With pyridine at 60℃; for 12h;
94%	With iron(III) chloride hexahydrate
90%	With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 80℃; for 29h;

Reference： [1]Hoffmann, Barbara; Zanini, Diana; Ripoche, Isabelle; Buerli, Roland; Vasella, Andrea [Helvetica Chimica Acta, 2001, vol. 84, # 6, p. 1862 - 1888]
[2]Location in patent: experimental part Ide, Yasuhiro; Hori, Yuji; Kobayashi, Soichi; Hossain, Md. Delwar; Kitamura, Tsugio [Synthesis, 2010, # 18, p. 3083 - 3086]
[3]Akae, Yosuke; Koyama, Yasuhito; Sogawa, Hiromitsu; Hayashi, Yoshihiro; Kawauchi, Susumu; Kuwata, Shigeki; Takata, Toshikazu [Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5335 - 5341]
[4]Akae, Yosuke; Sogawa, Hiromitsu; Takata, Toshikazu [European Journal of Organic Chemistry, 2019, vol. 2019, # 22, p. 3605 - 3613]
[5]Jicsinszky, Laszlo; Martina, Katia; Caporaso, Marina; Cintas, Pedro; Zanichelli, Andrea; Cravotto, Giancarlo [Physical Chemistry Chemical Physics, 2015, vol. 17, # 26, p. 17380 - 17390]
[6]Location in patent: experimental part Grachev; Edunov; Kurochkina; Popkov; Levina; Nifant'Ev [Russian Journal of Organic Chemistry, 2011, vol. 47, # 2, p. 284 - 289]

23
[ 502-65-8 ]
[ 10016-20-3 ]
C₄₀H₅₆*C₃₆H₆₀O₃₀ [ No CAS ]

Reference： [1]Carbohydrate Research,2002,vol. 337,p. 1129 - 1136

24
2^I,3^I,2^II,3^II,2^III,3^III,2^IV,3^IV,2^V,3^V,2^VI,3^VI-dodeca-O-benzyl-maltocyclohexaose [ No CAS ]
[ 10016-20-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol; water at 20℃; for 12h;

Reference： [1]Wakao, Masahiro; Fukase, Koichi; Kusumoto, Shoichi [Journal of Organic Chemistry, 2002, vol. 67, # 23, p. 8182 - 8190]

25
[ 723-62-6 ]
[ 10016-20-3 ]
poly(ethylene glycol), M_w 3.35E₃ Da [ No CAS ]
(polyethylene glycol)-(α-cyclodextrin) polyrotaxane, anthracene-terminated, M_w 2E4 Da [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.3%	Stage #1: anthracen-9-carboxylic acid; alpha cyclodextrin; poly(ethylene glycol), M_w 3.35E₃ Da In water at 20℃; Stage #2: With anthracen-9-carboxylic acid; benzotriazol-1-ol; triethylamine In water; N,N-dimethyl-formamide

Reference： [1]Okada, Miyuko; Harada, Akira [Macromolecules, 2003, vol. 36, # 26, p. 9701 - 9703]

26
[ 723-62-6 ]
[ 10016-20-3 ]
poly(ethylene glycol), M_w 2E₃ Da [ No CAS ]
(polyethylene glycol)-(α-cyclodextrin) polyrotaxane, anthracene-terminated, M_w 2.2E4 Da [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.3%	Stage #1: anthracen-9-carboxylic acid; alpha cyclodextrin; poly(ethylene glycol), M_w 2E₃ Da In water at 20℃; Stage #2: With anthracen-9-carboxylic acid; benzotriazol-1-ol; triethylamine In water; N,N-dimethyl-formamide

Reference： [1]Okada, Miyuko; Harada, Akira [Macromolecules, 2003, vol. 36, # 26, p. 9701 - 9703]

27
[ 100-44-7 ]
[ 10016-20-3 ]
hexakis-(2,3,6-tri-O-benzyl)-α-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydride In dimethyl sulfoxide at 20℃; for 22h; Inert atmosphere; Schlenk technique;
98%	In dimethyl sulfoxide at 20℃; Inert atmosphere;
95%	With sodium hydride In dimethyl sulfoxide at 20℃; for 18h;

95%	With sodium hydride In dimethyl sulfoxide
94%	With sodium hydride In dimethyl sulfoxide at 20℃; for 18h;
91%	With sodium hydride In dimethyl sulfoxide at 20℃;
90%	With sodium hydride; dimethyl sulfoxide at 20℃; for 12h;
89%	With sodium hydride In dimethyl sulfoxide at 20℃;
88%	Stage #1: alpha cyclodextrin With sodium hydride In dimethyl sulfoxide; mineral oil at 60℃; for 1h; Inert atmosphere; Stage #2: benzyl chloride In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere;
	With sodium hydride In dimethyl sulfoxide at 20℃;
	With sodium hydride In dimethyl sulfoxide at 20℃; for 18h;
	With sodium hydride

Reference： [1]Kurlemann, Michael; Ravoo, Bart Jan [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2428 - 2440]
[2]Location in patent: scheme or table Deunf, Elise; Zaborova, Elena; Guieu, Samuel; Bleriot, Yves; Verpeaux, Jean-Noel; Buriez, Olivier; Sollogoub, Matthieu; Amatore, Christian [European Journal of Inorganic Chemistry, 2010, # 29, p. 4720 - 4727]
[3]Lecourt, Thomas; Herault, Alexandre; Pearce, Alan J.; Sollogoub, Matthieu; Sinay, Pierre [Chemistry - A European Journal, 2004, vol. 10, # 12, p. 2960 - 2971]
[4]Rousseau, Cyril; Christensen, Brian; Petersen, Torben Ellebaek; Bols, Mikael [Organic and Biomolecular Chemistry, 2004, vol. 2, # 23, p. 3476 - 3482]
[5]Cui, Yanli; Mao, Jianwei; Mao, Yangyi; Zhang, Yongmin [RSC Advances, 2020, vol. 10, # 18, p. 10695 - 10702]
[6]Lopez, Oscar Lopez; Marinescu, Lavinia; Bols, Mikael [Tetrahedron, 2007, vol. 63, # 36, p. 8872 - 8880]
[7]Bertino-Ghera, Bernard; Perret, Florent; Fenet, Bernard; Parrot-Lopez, Helene [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7317 - 7326]
[8]Cherraben, Sawsen; Scelle, Jérémy; Hasenknopf, Bernold; Vives, Guillaume; Sollogoub, Matthieu [Organic Letters, 2021, vol. 23, # 20, p. 7938 - 7942]
[9]Warren, Julia; Bols, Mikael [European Journal of Organic Chemistry, 2019, vol. 2019, # 5, p. 1083 - 1091]
[10]López, Óscar; Bols, Mikael [Tetrahedron, 2008, vol. 64, # 32, p. 7587 - 7593]
[11]Location in patent: scheme or table Guieu, Samuel; Zaborova, Elena; Bleriot, Yves; Poli, Giovanni; Madec, David; Prestat, Guillaume; Sollogoub, Matthieu; Jutand, Anny [Angewandte Chemie - International Edition, 2010, vol. 49, # 13, p. 2314 - 2318][Angewandte Chemie, 2010, vol. 122, # 13, p. 2364 - 2368]
[12]Location in patent: scheme or table Lecourt, Thomas; Bleriot, Yves; Auzely-Velty, Rachel; Sollogoub, Matthieu [Chemical Communications, 2010, vol. 46, # 13, p. 2238 - 2240]
[13]Location in patent: scheme or table Bjerre, Jeannette; Bols, Mikael [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2011, vol. 69, # 3-4, p. 417 - 423]

28
[ 69839-68-5 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₆H₃₂O₂S [ No CAS ]

Reference： [1]New Journal of Chemistry,2005,vol. 29,p. 847 - 852

29
[ 38215-38-2 ]
[ 51839-16-8 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₃₂H₁₈O₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 7714 - 7715

30
[ 10016-20-3 ]
1-iodonaphthalene-3,6-disulfonic acid disodium salt [ No CAS ]
[ 338793-56-9 ]
(E)-4,4'-diiodo-stilbene-2,2'-disulfonate disodium salt [ No CAS ]
poly(diphenylene-vinylene) polyrotaxane, M_w 25800, n = 8.7; monomer(s): (E)-4,4'-diiodo-stilbene-2,2'-disulfonate disodium salt; (E)-4,4'-di([1,3,2]dioxaborolan-2-yl)-stilbene; 1-iodonaphthalene-3,6-disulfonate disodium salt; α-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium cyanide; lithium carbonate In water at 85℃;

Reference： [1]Michels, Jasper J.; O'Connell, Michael J.; Taylor, Peter N.; Wilson, Joanne S.; Cacialli, Franco; Anderson, Harry L. [Chemistry - A European Journal, 2003, vol. 9, # 24, p. 6167 - 6176]

31
[ 2595-90-6 ]
[ 10016-20-3 ]
[ 913976-28-0 ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 6701 - 6710

32
[ 432025-97-3 ]
[ 957420-97-2 ]
[ 10016-20-3 ]
[ 957421-10-2 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6845 - 6848

33
[ 432025-97-3 ]
[ 957421-04-4 ]
[ 10016-20-3 ]
[ 957421-17-9 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6845 - 6848

34
[ 432025-97-3 ]
[ 957421-06-6 ]
[ 10016-20-3 ]
2C₃₆H₆₀O₃₀*C₅₄H₃₂O₁₀ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6845 - 6848

35
C₁₈H₁₀O₄ [ No CAS ]
[ 51839-16-8 ]
[ 10016-20-3 ]
C₃₆H₁₈O₈ [ No CAS ]
[ 957421-10-2 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6845 - 6848

36
[ 2232-08-8 ]
[ 10016-20-3 ]
[ 93184-10-2 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 9185 - 9189

37
[ 6052-15-9 ]
[ 5400-70-4 ]
[ 10016-20-3 ]
[ 1020073-29-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 2496 - 2502

38
[ 108-69-0 ]
[ 10016-20-3 ]
[ 586-91-4 ]
C₃₀H₂₈N₄O₂*C₃₆H₆₀O₃₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	Stage #1: alpha cyclodextrin; azobenzene-4,4'-dicarboxylic acid In sodium sesquicarbonate at 20℃; for 2h; Stage #2: 3,5-dimethylaminoaniline With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In sodium sesquicarbonate at 20℃; for 10h;

Reference： [1]Maniam, Subashani; Cieslinski, Marta M.; Lincoln, Stephen F.; Onagi, Hideki; Steel, Peter J.; Willis, Anthony C.; Easton, Christopher J. [Organic Letters, 2008, vol. 10, # 10, p. 1885 - 1888]

39
[ 3638-04-8 ]
[ 1034911-52-8 ]
[ 10016-20-3 ]
[ 1034911-44-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1814 - 1821

40
[ 3638-04-8 ]
[ 621-96-5 ]
[ 10016-20-3 ]
[ 1034911-58-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1814 - 1821

41
[ 3638-04-8 ]
[ 538-41-0 ]
[ 10016-20-3 ]
[ 1034911-61-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1814 - 1821

42
n-dodecyl-β-D-maltotrioside [ No CAS ]
[ 74513-18-1 ]
[ 10016-20-3 ]
[ 59122-55-3 ]
[ 1190987-70-2 ]
[ 1190987-74-6 ]
dodecyl-β-D-maltoheptaoside [ No CAS ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1222 - 1226

43
n-decyl-β-D-maltopyranoside [ No CAS ]
[ 74513-18-1 ]
[ 7084-67-5 ]
[ 10016-20-3 ]
dodecyl-β-D-maltotetradecaoside [ No CAS ]
[ 1190987-76-8 ]
[ 1190987-70-2 ]
[ 1190987-80-4 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1222 - 1226

44
[ 74513-18-1 ]
[ 10016-20-3 ]
dodecyl-β-D-maltoeicosaoside [ No CAS ]
dodecyl-β-D-maltotetradecaoside [ No CAS ]
[ 1190987-70-2 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1222 - 1226

45
[ 1124-64-7 ]
[ 10016-20-3 ]
C₉H₁₄N⁽¹⁺⁾*C₃₆H₆₀O₃₀*Cl^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 6518 - 6529

46
[ 431-03-8 ]
[ 10016-20-3 ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: alpha cyclodextrin With pectin In water at 4.5 - 48℃; for 0.5h; Stage #2: dimethylglyoxal In water at 4.5℃; for 44h;	2 The β-cyclodextrin of example 1 was replaced with α-cyclodextrin and dry blended with 1 wt % pectin (i.e., 1 wt % of pectin: β-cyclodextrin; XPQ EMP 5 beet pectin available from Degussa-France). The mixture was processed and dried by the method set forth in Example 1. The percent retention of diacetyl in the cyclodextrin inclusion complex was 11.4 wt %.

Reference： [1]Current Patent Assignee: CARGILL, INCORPORATED - WO2006/137958, 2006, A1 Location in patent: Page/Page column 25

47
[ 20769-85-1 ]
[ 10016-20-3 ]
[ 1257082-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In chloroform at 0 - 20℃; for 24.5h; Inert atmosphere;
	With pyridine In chloroform at 0 - 20℃; for 24.5h; Inert atmosphere;	3 Synthesis of the Bromobutyryloxy α-Cyclodextrin (α-CD-BIBB) 2.3 Synthesis of the Bromobutyryloxy α-Cyclodextrin (α-CD-BIBB) A 250 mL round-bottom three-necked flask with a magnetic stirrer was charged with 6.48 g α-CD (6.67 mmol) and kept under nitrogen before the addition of 120 mL of dry pyridine. The system was cooled to 0 °C under stirring. A solution of 1.0 mL (8 mmol) 2-bromo-isobutyryl bromide (BIBB) in 40 mL of CHCl3 was slowly added within 30 min. Then, the reaction was continued at room temperature for 24 h. The mixture were washed with ice water several times to remove salts. And the organic layers were dried over anhydrous magnesium sulphate. The obtained white solids was washed with small amount of ice water again until the pH value reaches 7.0, then dried under vacuum at 40 °C to obtain α-CD-BIBB as white solids. FTIR (KBr pellet, cm-1): 1741 (-O-C=O), 3363 (O-H), 1366, 1332 (-C-CH3), 2930, 1407 (-CH2-), 630 (-Br). 1H NMR (D2O, ppm): 4.89-4.90 (6H, d, -CH(O-)2), 3.41-3.83 (42H, -OH, =CHO-, -CH2O-), 1.72 (6H, -CH3). Element analysis: theoretical value: C 42.83%, H 5.84%, Br 7.12%; Found: C 42.96%, H 5.99%.

Reference： [1]Location in patent: experimental part Yao, Fang; Xu, Li Qun; Fu, Guo-Dong; Lin, Bao Ping [Macromolecules, 2010, vol. 43, # 23, p. 9761 - 9770]
[2]Zhou, Yingxue; Fan, Xiaodong; Xue, Dan; Xing, Jianwei; Kong, Jie [Reactive and functional polymers, 2013, vol. 73, # 3, p. 508 - 517]

48
[ 108-24-7 ]
[ 106-95-6 ]
[ 10016-20-3 ]
per-O-acetyl-2-O-allyl-α-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	Stage #1: alpha cyclodextrin With lithium hydride In dimethyl sulfoxide for 24h; Inert atmosphere; Stage #2: allyl bromide With lithium iodide In dimethyl sulfoxide for 2h; Inert atmosphere; Stage #3: acetic anhydride With triethylamine at 80℃;	4.2.1. Per-O-acetyl-2^I-O-allyl-α-cyclodextrin (3a) Firstly, the synthesis was carried out according to the exactly the same reaction conditions as described by Hanessian et al.refPreviewPlaceHolder10 The results were the same as described below, but the procedure was inconvenient. Thus the procedure was improved as follows: Dried α-cyclodextrin (880 mg, 910 μmol) was dissolved in dry DMSO (9 mL), and lithium hydride was added (11 mg, 1.4 mmol). The reaction mixture was stirred under an Ar atmosphere for 24 h. Then allyl bromide (79 μL, 910 μmol) and lithium iodide (3 mg, 24 μmol) were added to the reaction mixture. The reaction was monitored by TLC (6:3:1:1 1-PrOH-H2O-EtOAc-aq NH3) and was determined finished after 2 h when no significant increase in monosubstituted derivatives was observed. The CD derivatives were precipitated with acetone (170 mL), filtered out, and washed with acetone (50 mL). The precipitate was adsorbed on silica gel (3.5 g), and mono-O-allyl-α-CDs were separated by chromatography on a silica gel column (7:3:2 1-PrOH-H2O-EtOAc-aq NH3). The mixture of mono-O-allyl-α-CDs was then peracetylated. A suspension of mono-O-allyl-α-CDs in Ac2O (2.2 mL, 24 mmol) and Et3N (2.2 mL, 16 mmol) was stirred at 80 °C overnight. The reaction mixture was diluted with CHCl3, washed with 5% HCl, and the organic layer was evaporated in vacuo to give a brown residue that was purified by chromatography on silica gel (100:1 CHCl3-MeOH). Workup afforded 420 mg (27% overall yield based on α-CD) of the title compound as a white powder: mp 139-141 °C. +98 (CHCl3). IR (KBr): ν = 1747, 1372, 1238, 1040 cm-1. 1H NMR (300 MHz, CDCl3): δ 5.81 (ddt, 1H, J2',3'a 17.1, J2',3'b 10.4, J2',1' 5.7 Hz, H-2'), 5.73 (dd, 1H, J2,3 10.2, J3,4 8.9 Hz, H-3), 5.64 (dd, 1H, J2,3 10.6, J3,4 9.0 Hz, H-3), 5.59 (dd, 1H, J2,3 10.3, J3,4 8.7 Hz, H-3), 5.50 (dd, 1H, J2,3 10.1, J3,4 8.7 Hz, H-3), 5.46 (dd, 1H, J2,3 10.2, J3,4 8.7 Hz, H-3), 5.32 (dd, 1H, J2,3 9.8, J3,4 9.1 Hz, H-3I), 5.24 (dq, 1H, J2',3'a 17.2, J1',3'a = J3'a,3'b 1.5 Hz, H-3'a), 5.19 (dq, 1H, J2',3'b 10.3, J1',3'b = Jgem 1.2 Hz, H-3'b), 5.14 (d, 1H, J1,2 3.5 Hz, H-1), 5.11 (d, 1H, J1,2 3.6 Hz, H-1), 5.09 (d, 1H, J1,2 3.8 Hz, H-1), 4.99 (d, 1H, J1,2 2.9 Hz, H-1), 4.99 (d, 1H, J1,2 3.1 Hz, H-1), 4.87 (d, 1H, J1,2 3.2 Hz, H-1I), 4.82 (dd, 1H, J2,3 10.3, J1,2 3.9 Hz, H-2), 4.81 (dd, 1H, J2,3 10.7, J1,2 3.7 Hz, H-2), 4.77 (dd, 1H, J2,3 10.4, J1,2 3.6 Hz, H-2), 4.77 (dd, 1H, J2,3 10.2, J1,2 3.5 Hz, H-2), 4.71 (dd, 1H, J2,3 10.2, J1,2 3.8 Hz, H-2), 4.60-4.05 (m, 18H, 6 × H-5, 12 × H-6), 4.03-3.99 (m, 2H, 2 × H-1'), 3.85-3.77 (m, 4H, 4 × H-4), 3.74 (t, 1H, J3,4 = J4,5 9.2 Hz, H-4), 3.66 (t, 1H, J3,4 = J4,5 9.2 Hz, H-4I), 3.32 (dd, 1H, J2,3 10.1, J2,3 3.1 Hz, H-2I), 2.30-1.98 (m, 51H, 17 × CH3). 13C NMR (101 MHz, CDCl3): δ 170.90-169.01 (17 × CO), 134.46 (C-2'), 117.76 (C-3'), 98.68 (C-1I), 97.19 (C-1), 96.70 (C-1), 96.58 (C-1), 96.38 (C-1), 95.82 (C-1), 79.58-68.73 (5 × C-2, 5 × C-3, 5 × C-4, 6 × C-5), 78.06 (C-4I), 77.96 (C-2I), 72.87 (C-3I), 72.13 (C-1'), 63.40-62.89 (6 × C-6), 20.94-20.62 (17 × CH3). HRESIMS: [M+Na]+, found 1749.5146. C73H98O47Na requires 1749.5171.

Reference： [1]Location in patent: experimental part Řezanka, Michal; Jindřich, Jindřich [Carbohydrate Research, 2011, vol. 346, # 15, p. 2374 - 2379]

49
[ 106-95-6 ]
[ 10016-20-3 ]
C₇₅H₁₁₂O₃₀ [ No CAS ]
[ 114868-55-2 ]

Yield	Reaction Conditions	Operation in experiment
40%	With barium hydroxide octahydrate; barium(II) oxide In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 120h; Inert atmosphere;	4.3. Cyclohexakis-(1→4)-2,6-di-O-allyl-α-d-glucopyranosyl [per(2,6-di-O-allyl)-α-cyclodextrin] The compound was prepared from α-cyclodextrin (3 g, 3.1 mmol), using the procedure described for 4β. Column chromatography (SiO2, 40:60 EtOAc-CHCl3) afforded a white solid (1.8 g, 40%) that was characterized as per(2,6-di-O-allyl)-α-cyclodextrin (α). 1H NMR (300 MHz, DMSO-d6): δ 5.81-5.96 (m, 12Hb), 5.11-5.34 (m, 24Hc), 4.95 (d, 6H1), 4.56 (s, 6OH3), 3.30-4.35 (m, 24Ha, 6H5, 6H3, 6H6, 6H4, 6H2); 13C NMR (75 MHz, CDCl3): δ 68.82 (C6), 70.40 (C5), 73.68 (C3), 72.65, 73.24 (Ca), 78.65 (C2), 83.52 (C4), 101.50 (C1), 117.37, 118.75 (Cc), 134.23, 134.85 (Cb); ESIMS: m/z 749.5 (M+2Na)2+, 1476.4 (M+Na)+.

Reference： [1]Location in patent: experimental part Eskandani, Zahra; Huin, Cécile; Guégan, Philippe [Carbohydrate Research, 2011, vol. 346, # 15, p. 2414 - 2420]

50
[ 74513-18-1 ]
[ 10016-20-3 ]
[ 1190987-70-2 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2011,vol. 69,p. 147 - 153

51
[ 74513-18-1 ]
[ 10016-20-3 ]
[ 1190987-70-2 ]
n-dodecyl (1,4)-β-maltotetradecaoside [ No CAS ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2011,vol. 69,p. 147 - 153

52
[ 10016-20-3 ]
[ 480-18-2 ]
[ 1310728-92-7 ]

Reference： [1]Carbohydrate Polymers,2011,vol. 85,p. 629 - 637

53
[ 10016-20-3 ]
[ 83881-52-1 ]
C₂₁H₂₅ClN₂O₃*C₃₆H₆₀O₃₀*2ClH [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,2011,vol. 100,p. 3177 - 3185

54
[ 7173-51-5 ]
[ 10016-20-3 ]
C₂₂H₄₈N⁽¹⁺⁾*2.5C₃₆H₆₀O₃₀*Cl^(1-) [ No CAS ]

Reference： [1]European Journal of Pharmaceutical Sciences,2012,vol. 46,p. 336 - 345

55
[ 1968-05-4 ]
[ 10016-20-3 ]
[ 1426131-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; aq. phosphate buffer; at 24.99℃;pH 7.2;	General procedure: The inclusion complex formation phenomenon of CDs with guest DIMs in aqueous phosphate buffer solutions was examined at pH 7.2 by means of UV?visible spectral titration in a Shimadzu 1700 Spectrophotometer (Shimadzu Corporation, Kyoto, Japan). A 1.0 mM stock solution of DIMs (5.0 ml) was prepared in methanol, and 6.0 ll of this stock solution was added to the phosphate buffer solution to maintain the final concentration of molecules as 2.5 10 7 mol dm 3 in the cuvette. Then gradually a-, b-, c-CD were added in the cuvette so that the concentrations of CDs ranged from 0 to 12.5 10 3 mol dm 3. The absorption spectra were measured against an appropriate reagent blank.

Reference： [1]Journal of Molecular Structure,2013,vol. 1036,p. 1 - 6

56
[ 84562-48-1 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₀H₁₃NO₂ [ No CAS ]
2C₃₆H₆₀O₃₀*C₁₀H₁₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water

Reference： [1]Samanta, Anuva; Jana, Sankar; Guchhait, Nikhil [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013, vol. 75, # 1-2, p. 57 - 68]

57
[ 67373-56-2 ]
[ 10016-20-3 ]
C₈₄H₁₆₈O₃₀Si₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine at 0℃; for 2h;	4.1.1 Per-6-O-dimethylthexylsilyl-α-CD (3) General procedure: To a solution of anhydrous α-CD 1 (5.0g, 5.14mmol) in dry pyridine (300mL) at 0°C wasadded dropwise dimethylthexylsilyl chloride (13.34mL, 67.8mmol). The mixture was stirred for 2h at 0°C, and then allowed to room temperature. The reaction was monitored by TLC (butanone-1-butanol-water, 9:1:1; Rf 0.50), and it was completed after 40h. Solvent was evaporated under reduced pressure, a solution of the residue in chloroform (250mL) was washed with water and dried, and the solvent was evaporated. The residue was recrystallized from MeOH-CHCl3 to give 3 (7.85g, 83% yield). 1H NMR (400MHz, CDCl3): δ 6.53 (s, 6H, 6× OH), 5.30 (s, 6H, 6× OH), 4.89 (d, 6H, J=3.0Hz, 6× H-1), 4.04 (dd, 6H, J=8.9, 9.0Hz, 6× H-3), 3.92 (dd, 6H, J=2.7, 11.4Hz, 6× H-6a), 3.81 (m, 6H, 6× H-5), 3.92 (dd, 6H, J=∼1.0, 10.8Hz, 6× H-6b), 3.64 (m, 12H, 6× H-2+6× H-4), 1.62 (septet, 6H, J=6.8Hz, 6× (CH3)2CHC(CH3)2Si), 0.90-0.85 (4× s, 72H, 6× (CH3)2CHC(CH3)2Si+6× (CH3)2CHC(CH3)2Si), 0.09 (m, 36H, 6× (CH3)2Si). 13C NMR (100MHz, CDCl3): δ 101.4 (6× C-1), 81.4 (6× C-2), 74.4 (6× C-3), 73.1 (6× C-5), 72.3 (6× C-4), 61.6 (6× C-6), 34.2 (6× (CH3)2CHC(CH3)2Si), 25.2 (6× (CH3)2CHC(CH3)2Si), 20.4, 20.3, 18.6, 18.5 (6× (CH3)2CHC(CH3)2Si+6× (CH3)2CHC(CH3)2Si), -3.26, -3.3 (6× (CH3)2Si).

Reference： [1]Ghosh, Ramprasad; Hennigan, Cormac; Ling, Chang-Chun [Tetrahedron, 2013, vol. 69, # 25, p. 5227 - 5233]

58
[ 134-03-2 ]
[ 10016-20-3 ]
[ 129499-78-1 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 92,p. 19 - 23

59
[ 77-92-9 ]
[ 10016-20-3 ]
poly(citric acid-α-cyclodextrin) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hypophosphite monohydrate at 140℃; for 0.5h;	Synthesis of poly-(cyclo)dextrins General procedure: Water soluble polymers of MD, α-CD, β-CD, γ-CD, HPβCD and MβCD, respectively named polyCTR-MD, polyCTR-αCD, polyCTR-βCD, polyCTR-γCD, polyCTR-HPβCD and polyCTR-MβCD, were synthesized as previously reported (Martel et al., 2002; Martel, Ruffin, Weltrowski, Lekchiri, & Morcellet, 2005). Briefly, aqueous solutions (200 mL) of sodium dihydrogen hypophosphite (30 g/L), CTR (100 g/L) and the corresponding CD or MD (100 g/L) were prepared under stirring at room temperature. Water was totally removed from the solutions using a Rotavapor (Büchi, Switzerland). The resulting dried mixture was then heated at 140 °C in oil bath during 30 min also under vacuum (∼60 mbar). The polymer was redispersed in water (200 ml) and then filtered on sintered glass funnel to remove the insoluble fraction. The filtrate was concentrated in rotavapor and dialyzed (6000-8000 MWCO) against water (2 L, exchanged every 12 h) for 3 days. Finally, the polymer was recovered as a white powder by freeze-drying. The yield of each polymer fraction (soluble and gel) was calculated as the ratio of the weight of the obtained product to the weight of CTR plus CD in the initial solution. The catalyst was neglected as only traces of phosphorus were detected by elemental analysis in the final product

Reference： [1]García-Fernández; Tabary; Martel; Cazaux; Oliva; Taboada; Concheiro; Alvarez-Lorenzo [Carbohydrate Polymers, 2013, vol. 98, # 2, p. 1343 - 1352]

60
[ 4478-93-7 ]
[ 10016-20-3 ]
[ 1498229-87-0 ]

Yield	Reaction Conditions	Operation in experiment
78.5%	Stage #1: alpha cyclodextrin In water at 55℃; Inert atmosphere; Cooling with ice; Stage #2: D,L-sulforaphane In water at 20℃; for 16h;	2 a-Cyclodextrin (Wacker CAVAMAX W6 Food Grade, 3015g, 3.1 moles, 1 equivalent) was dissolved in distilled water (8L) by heating up to 55°C under nitrogen atmosphere. Thehomogeneous solution was cooled down to - 25°C using an ice-water bath and then degassed for-20 min by purging nitrogen. After degassing, it turned into a foggy solution. Aqueous solutionof sulforaphane was removed from the refrigerator (see previous step) and then added to theabove foggy a-cyclodextrin solution at once. At this stage reaction temperature was -18°C, and continued stirring at room temperature overnight ( -16h). The heterogeneous reaction mixturewas cooled down to 1-2 °C using ice-methanol bath and stirred for 3 hr at that temperature. Theprecipitated white solid was filtered and dried overnight under high vacuum at room temperatureby covering the filter funnel with a latex sheet. The white filter cake was transferred into a 10-Lrotovap flask and dried further at room temperature under a high vacuum to afford 2,802g of complex (98.7% pure by HPLC, 78.5% yield). All three batches were conducted at almost same scale and the reactions proceeded in similar way in terms of reaction time, yield, product purity and percentage loading ofsulforaphane on a-cyclodextrin 1HNMR (D20, 400 MHz); 81.99 (br, 4H), 2.73 (s, 3H), 2.98 (br, 2H), 3.60 (m, 12H), 3.70(br, 2H), 3.92(m, 24H), 5.11 (d, 6H). 13 CNMR (D20, 100 MHz); u~ 130.05, 101.82, 81.40, 74.05, 71.98, 71.84, 60.34, 52.02,44.94, 37.03, 29.29, 20.08..11 (d, 6H).
76.9%	With dihydrogen peroxide In water at 0 - 55℃; Large scale;	1; 1A; 4 Example 1A: Formation of a complex of sulforaphane and α-cyclodextrin according to procedures in WO 2013/179057 To degassed a-cydodextrin (30 g, 0.01 eqv) in water (1 L) at room temperature was added 1-isothiocyanato-4-methylthiobutane (501 g, 1 eqv). The solution was cooled to 0°C and degassed for 30 mins. To the suspension was added 35% aqueous H2O2 (305 mi, 1 eqv) slowly while maintaining the internal temp below 4°C during the addition. The reaction mixture was stirred for 8 hr at ice bath temperature and was then allowed to warm to room temperature while stirring overnight. The solution was filtered to remove solids. The filtrate was refrigerated for 5 hr prior to use in the next step. α-cyclodextrin (3015 g, 1 eqv) was dissolved in water (8 L) by heating up to 55 °C, The solution was cooled down to room temperature and the sulforaphane filtrate from the previous step was added at once. The mixture was stirred at room temperature overnight. The reaction mixture was then cooled in an ice bath and stirred at that temperature for 3 hr. The precipitated solid was filtered through Buchner funnel and dried on the filter under vacuum overnight. The filter cake was transferred to a 10 L round-bottomed flask and dried under high vacuum at room temperature over the weekend to yield a white soiid (2.74 kg, 76.9% yieid; batch ref. 191PAL79). The soiid had a water content of 11.3% w/w by Karl-Fischer analysis and a purity by HPLC of 98.5%. 1-NMR analysis confirmed that Example 1A was a 1:1 sulforaphane:α-cyclodextrin complex.

Reference： [1]Current Patent Assignee: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD. - WO2013/179057, 2013, A1 Location in patent: Paragraph 00107; 00108; 00109; 00110
[2]Current Patent Assignee: EVGEN PHARMA - WO2021/205171, 2021, A1 Location in patent: Paragraph 0123-0124; 0126-0127; 0139-0139

61
[ 197153-87-0 ]
[ 10016-20-3 ]
[ 1544169-52-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1725 - 1727

62
[ 80-35-3 ]
[ 10016-20-3 ]
[ 1569300-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; at 50℃;	General procedure: CD (1 mmol) was dissolved in 30 ml distilled water and SMP (1 mmol) in 20 ml methanol and was slowly added to the CD solution. This solution was stirred at 50 C overnight. The above solution was refrigerated overnight at 5 C. The precipitated SMP/CD complexes were recovered by filtration and washed with a small amount of ethanol and water to remove uncomplexed drug and CD, respectively. This precipitate was dried in vacuum at room temperature for two days and stored in an air tight bottle. This powder sample was used for further analysis.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 123,p. 158 - 166

63
[ 82419-36-1 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₈H₂₀FN₃O₄ [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2013,vol. 77,p. 291 - 300

64
[ 127-79-7 ]
[ 10016-20-3 ]
[ 1581737-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; at 50℃; for 24h;	General procedure: alpha-CD/beta-CD (0.9728/1.135g) was dissolved in 40ml distilled water at 50C in a water bath. SMRZ (0.264g) in 10ml methanol was slowly added to the CD solution with continuous agitation. The molar ratio of SMRZ to CDs was 1:1. The vessel covered with aluminum foil and stirred continuously for 24h. Then the final solution was refrigerated overnight at 5C. The precipitated SMRZ/CDs complexes were recovered by filtration and washed with small amount of methanol and water to remove uncomplexed drug and CDs, respectively. This precipitate was dried in vacuum at room temperature for two days and stored in an airtight bottle. This powder samples were further analyzed by using FT-IR,1H NMR, DSC, XRD and SEM methods.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 124,p. 441 - 450

65
[ 10016-20-3 ]
[ 1689-82-3 ]
C₃₆H₆₀O₃₀*C₁₂H₁₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water at 50℃;	Preparation of Nanomaterials General procedure: CD (1mmol) was dissolved in 40 mL of distilled water and DHAB or HAB (1 mmol) in 10 mL of methanol and was slowly added to the CD solution. This mixture was stirred at 50 °C overnight. Then the final solution was refrigerated overnight at 5 °C. The precipitated DHAB/CD and HAB/CD complexes were recovered by filtration and washed with a small amount of ethanol and water to remove uncomplexed DHAB, HAB, and CD, respectively. This precipitate was dried in vacuum at room temperature for two days and stored in an airtight bottle. This powder sample was used for further analysis.

Reference： [1]Venkatesh, Govindaraj; Saravanan, Jayachandran; Rajendiran, Narayanasamy [Bulletin of the Chemical Society of Japan, 2014, vol. 87, # 2, p. 283 - 293]

66
[ 94-13-3 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₀H₁₂O₃ [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2014,vol. 79,p. 365 - 381

67
[ 94-26-8 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₁H₁₄O₃ [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2014,vol. 79,p. 365 - 381

68
[ 7173-51-5 ]
[ 10016-20-3 ]
α-cyclodextrin 1:1 complex with di-n-decyldimethylammonium chloride [ No CAS ]
α-cyclodextrin 2:1 complex with di-n-decyldimethylammonium chloride [ No CAS ]

Reference： [1]Langmuir,2013,vol. 29,p. 6242 - 6252

69
[ 105816-04-4 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₉H₂₇NO₃ [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2836 - 2843

70
[ 5578-73-4 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₂₀H₁₄NO₄⁽¹⁺⁾ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 1873 - 1882

71
[ 27208-80-6 ]
[ 10016-20-3 ]
trans-resveratrol-3-O-β-D-diglucoside [ No CAS ]
C₃₂H₄₂O₁₈ [ No CAS ]
C₃₈H₅₂O₂₃ [ No CAS ]
C₄₄H₆₂O₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With cyclodextrin glucanotransferase; In aq. buffer; for 24h;pH 5.4;	Production Example 1 400 mg of trans-resveratrol-3-O-beta-D-monoglucoside, 4 g of alpha-cyclodextrin, and 25 mL of Cyclodextrin glucanotransferase ?Amano? (600 units/mL; Amano Enzyme Inc.) were added to 300 mL of citric acid-sodium citrate buffer (pH of 5.4), and the mixture was stirred by a magnetic stirrer in a hot-water bath at 55 C. for 24 hours to perform enzyme reaction. [0133] Subsequently, the reaction solution was heated to 80 C. in a hot-water bath to inactivate the Cyclodextrin glucanotransferase ?Amano?. The reaction solution was then cooled to ordinary temperature, and partition extraction with ethyl acetate/water was performed six times. The obtained oil phase fraction was subjected to salting-out, dehydration, and a vacuum concentration process, and sampled by HPLC using a CrestPak C18S column (JASCO; 4.6×150). [0134] The aqueous phase fraction obtained by partition extraction with ethyl acetate was further subjected to partition extraction with water-saturated n-butanol three times, and then to a vacuum concentration process. Subsequently, fractionation was performed by HPLC using a CrestPak C18S column (JASCO; 4.6×150), and each fraction was sampled. The HPLC was performed for 40 minutes under the following conditions: column temperature: 40 C., mobile phase: a mixture of acetonitrile and water (15:85), flow rate: 1.0 m/min, and injection amount: 5 muL. [0135] FIG. 1 shows the results of column chromatography by HPLC of the reactant obtained by using trans-resveratrol-3-O-beta-D-monoglucoside as a starting material. FIG. 1 (A) is the column chromatogram of the oil phase fraction after phase separation with ethyl acetate/water, and (B) is the column chromatogram of the aqueous phase fraction. [0136] As shown in FIG. 1 (A), only a single peak was obtained from the oil phase fraction, whereas (B) shows that prominent peaks, which indicated that sugar units were added to the trans-resveratrol-3-monoglucoside to produce polysaccharides with 2 to 5 sugars, were detected on the basis of the difference in retention time by HPLC (fractions indicated by (a) to (d)). Further, the production of polysaccharides with 6 to 9 sugars was also detected (fraction (e)). [0137] The fraction (a), which showed the longest retention time (horizontal axis of the graph) in the column chromatogram by HPLC of the oil phase fraction, was subjected to NMR measurement. The frequency of the apparatus used was 400 MHz. FIG. 2 shows the results. [0138] From the results shown in FIG. 2 (A), this fraction was identified as trans-resveratrol-3-O-beta-D-diglucoside shown in (B). These results also suggested that the fraction showing a single peak in FIG. 1 (A) was trans-resveratrol-3-O-beta-D-monoglucoside, which was a starting material. [0139] Further, the fraction (a) and the fraction (b), which showed the second-longest retention time, were combined and subjected to MS measurement. FIG. 5 shows the results. The obtained results matched the molecular weights of trans-resveratrol-3-O-beta-D-diglucoside and a polysaccharide in which two molecules of glucose were added to trans-resveratrol-3-O-beta-D-monoglucoside. [0140] FIG. 6 shows the results when the fractions (c) and (d) were similarly subjected to MS measurement. The obtained results of these fractions matched the molecular weights of a polysaccharide in which three molecules of glucose were added to trans-resveratrol-3-O-beta-D-monoglucoside, and a polysaccharide in which four molecules of glucose were added to trans-resveratrol-3-O-beta-D-monoglucoside. [0141] The above results revealed that although trans-resveratrol monoglucoside was not dissolved in water at ordinary temperature, polysaccharides in which one or more glucose molecules were further added to trans-resveratrol monoglucoside (e.g., trans-resveratrol-3-O-beta-D-diglucoside), etc., could acquire water solubility at ordinary temperature. [0142] FIG. 7 is a photographic image showing trans-resveratrol-3-O-beta-D-monoglucoside contained in the fraction showing a single peak detected in FIG. 1 (A), and trans-resveratrol-3-O-beta-D-diglucoside contained in the fraction (a) in FIG. 1 (B), after they were dissolved in distilled water and allowed to stand at room temperature. [0143] As is clear from the figure, the tube of the trans-resveratrol-3-O-beta-D-monoglucoside was turbid (on the right side of the photographic image), indicating that it was not dissolved in distilled water at room temperature, whereas the tube of the trans-resveratrol-3-O-beta-D-diglucoside was transparent (on the left side of the photographic image), indicating that it was easily dissolved in distilled water at room temperature. [0144] The retention time of cis-resveratrol by column chromatography is known to tend to be longer than that of trans-resveratrol; however, the results of the above chromatogram showed no detection of cis-resveratrol.

Reference： [1]Patent: US2015/98987,2015,A1 .Location in patent: Paragraph 0132; 0133; 0134; 0135; 0136; 0137; 0138; 0139

72
[ 106-96-7 ]
[ 10016-20-3 ]
mono-2-O-propargyl-α-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: alpha cyclodextrin With lithium hydride In dimethyl sulfoxide Stage #2: propargyl bromide With lithium iodide In dimethyl sulfoxide at 55℃; Darkness;	Mono-2-propargyl-β-CD General procedure: To a solution of dry β-CD (10g, 10 mmol) in DMSO (100 ml) LiH (1 eq) was added and stirred overnight, until solution became clear. Next, propargyl bromide (1 eq) and LiI (spatula point) were added and the mixture was stirred at 55 °C for 5h, avoiding light exposition. Solvent was evaporated under reduced pressure, resulting slurry was dissolved in water (20 ml) and precipitated with acetone (500 ml). Solid residue was filtered, air-dried and resulting powder was dissolved in water and passed through styrene resin (Diaion HP-20) using gradient of water/methanol (0 to 10%) as solvent. Prior to use,resin was conditioned in methanol for 1 h and rinsed with water. Fractions containing pure product were evaporated under reduced pressure giving 4,1g of 4. The analytical data were in accord with literature values (Casas-Solvas,J.; Ortiz-Salmcron, E.; Fernandez, I.;Garcia-Fuentes, L.; Santoyo-Gonzales, F.; Vargas-Berenguel, A. Chem. DM J. 2009, 15,8146- 8162)

Reference： [1]Chmurski, Kazimierz; Stepniak, Pawel; Jurczak, Janusz [Synthesis, 2015, vol. 47, # 13, p. 1838 - 1843]

73
[ 2530-83-8 ]
[ 10016-20-3 ]
C₄₅H₈₀O₃₅Si [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 66674 - 66680

74
[ 14933-08-5 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₇H₃₇NO₃S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2016,vol. 214,p. 264 - 269

75
[ 84942-40-5 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₈H₆ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water

Reference： [1]Gashnga, Pynsakhiat Miki; Singh, T. Sanjoy; Mitra, Sivaprasad [Journal of Molecular Liquids, 2016, vol. 218, p. 549 - 557]

76
[ 58909-39-0 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₄H₅N₃O₂S [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 82817 - 82823

77
[ 75706-12-6 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₂H₉F₃N₂O₂ [ No CAS ]

Reference： [1]Thermochimica Acta,2016,vol. 642,p. 10 - 16

78
[ 24169-02-6 ]
[ 10016-20-3 ]
C₁₈H₁₅Cl₃N₂O*HNO₃*C₃₆H₆₀O₃₀ [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,2018,vol. 107,p. 1342 - 1351

79
4-(2-(4-((6-cyclohexyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)amino)-1H-pyrazol-1-yl)ethoxy)-4-oxobutanoic acid [ No CAS ]
[ 10016-20-3 ]
C₆₈H₁₀₃N₇O₄₃ [ No CAS ]
C₆₈H₁₀₃N₇O₄₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 14% 2: 17%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	γ-cyclodextrin conjugates 18 and 19. 4-(2-(4-((6-Cyclohexyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)amino)-1H-pyrazol-1-yl)ethoxy)-4-oxobutanoic acid (460 mg, 1.08 mmol), EDC (289mg, 1.51 mmol), γ-cyclodextrin (2.79 g, 2.152 mmol) and DMAP (26.3 mg, 0.215 mmol) were combined. DMF (3.0 mL) was added and the reaction mixture was stirred at ambient temperature overnight. Acetone (20 mL) was added to the reaction mixture and the resultingsuspension was filtered and rinsed with additional acetone (2 x 10 mL). The collected solid waspurified via HPLC-MS to yield two products as white solids, 2-O-γ-cyclodextrin conjugate 18(258 mg, 14%); MS m/z: 1707 (M+H)+ 1H NMR (400 MHz, DMSO-d6) δ 10.14 (s, 1H), 8.47 (s,1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.92 (s, 1H), 6.06±5.36 (m, 16H), 5.13 (d, J = 3.8 Hz, 1H), 4.95±4.78 (m, 7H), 4.74±4.39 (m, 8H), 4.36 (s, 4H), 3.84±3.75 (m, 1H), 3.70±3.43 (m, 30H), 3.44±3.11 (m, 16H), 2.74±2.51 (m, 5H), 1.92 (d, J = 11.9 Hz, 2H), 1.82 (d, J = 12.6 Hz, 2H), 1.73 (d,J = 12.1 Hz, 1H), 1.65±1.51 (m, 2H), 1.39 (q, J = 12.5 Hz, 2H), 1.32±1.20 (m, 1H). 6-O-γ-cyclodextrinconjugate 19 (315 mg, 17%); MS m/z: 1707 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ10.13 (s, 1H), 8.47 (s, 1H), 8.15 (s, 1H), 8.03 (s, 1H), 7.90 (s, 1H), 5.75 (br s, 16H), 4.89±4.84(m, 8H), 4.46 (br s, 8H), 4.35 (s, 4H), 4.31±4.16 (m, 2H), 4.15±4.07 (m, 1H), 3.84±3.72 (m,1H), 3.70±3.44 (m, 29H), 3.41±3.30 (m, 14H), 2.63±2.50 (m, 5H), 1.92 (d, J = 12.0 Hz, 2H),1.82 (d, J = 12.8 Hz, 2H), 1.73 (d, J = 12.4 Hz, 1H), 1.68±1.50 (m, 2H), 1.38 (q, J = 12.6 Hz, 2H),1.32±1.22 (m, 1H).

Reference： [1]George, Dawn M.; Huntley, Raymond J.; Cusack, Kevin; Duignan, David B.; Hoemann, Michael; Loud, Jacqueline; Mario, Regina; Melim, Terry; Mullen, Kelly; Somal, Gagandeep; Wang, Lu; Edmunds, Jeremy J. [PLoS ONE, 2018, vol. 13, # 9]

80
4-((4-(4-((6-cyclohexyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)amino)-1H-pyrazol-1-yl)-2-methylbutan-2-yl)oxy)-4-oxobutanoic acid [ No CAS ]
[ 10016-20-3 ]
C₅₉H₈₉N₇O₃₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 17h;	α-cyclodextrin conjugate 20 4-((4-(4-((6-Cyclohexyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)amino)-1H-pyrazol-1-yl)-2-methylbutan-2-yl)oxy)-4-oxobutanoic acid (0.200 g, 0.426 mmol),α-cyclodextrin (0.829 g, 0.852 mmol) and N,N-dimethylpyridin-4-amine (10.4 mg, 0.085mmol) were combined with DMF (4.0 mL). EDC (0.122 g, 0.639 mmol) was added and there action mixture was stirred at ambient temperature for 17 h. Acetone (5 mL) was added andthe resultant precipitate was filtered. The collected solid was purified by HPLC-MS to providethe α-cyclodextrin conjugate 20 (0.140 g, 23%); MS m/z: 1425 (M+H)+. 1H NMR (400 MHz,DMSO-d6) δ 10.11 (s, 1H), 8.47 (s, 1H), 8.18 (s, 1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.83 (s, 1H),5.60±5.34 (m, 12H), 4.84±4.74 (m, 7H), 4.45 (br s, 5H), 4.34±4.27 (m, 1H), 4.25 (s, 1H), 4.21±4.10 (m, 2H), 3.89±3.82 (m, 1H), 3.81±3.72 (m, 7H), 3.71±3.52 (m, 16H), 3.47±3.30 (m, 10H),2.69±2.57 (m, 1H), 2.55±2.49 (d, J = 6.7 Hz, 3H), 2.29±2.17 (m, 2H) δ 1.91 (d, J = 10.9 Hz, 2H),1.82 (d, J = 12.8 Hz, 2H), 1.73 (d, J = 12.2 Hz, 1H), 1.59 (q, J = 12.1, 10.9 Hz, 2H), 1.46±1.33(m, 8H), 1.32±1.18 (m, 1H).

Reference： [1]George, Dawn M.; Huntley, Raymond J.; Cusack, Kevin; Duignan, David B.; Hoemann, Michael; Loud, Jacqueline; Mario, Regina; Melim, Terry; Mullen, Kelly; Somal, Gagandeep; Wang, Lu; Edmunds, Jeremy J. [PLoS ONE, 2018, vol. 13, # 9]

81
[ 10016-20-3 ]
[ 174501-64-5 ]
C₃₆H₆₀O₃₀*F₆P^(1-)*C₈H₁₅N₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 80℃; for 4h;	General procedure: Aqueous CD solutions were prepared by adding the solidCD to water and ultrasonicating the mixture for 30 min.To obtain the ICs, the IL was added to the mixture, followedby heat treatment at 80 C in a water bath for 4 h andfinally 30 min of further ultrasonication. The concentrationsof CD and ILs in each aqueous IC solution are provided inTable 1. The ICs are named according to the constituent CDand IL: A and B refer to alpha- and beta-CD, respectively, whilethe number indicates the alkyl chain length of the cation ofthe IL. A separate gel-like phase was obtained for all fourICs (shown in Online Resource 1). In the case of B12, theIC phase precipitated out spontaneously during preparation.A4, A12, and B4 IC phases appeared several weeks afterpreparation. The IC phases were separated from the aqueoussolution and dried by heating to 80 C. While the IC phaseswere white/translucent in solution, they turned dark whenseparated from the solution and/or dried.

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2018,vol. 92,p. 301 - 309

82
1,2-O,O'-diacetyllycorine [ No CAS ]
[ 10016-20-3 ]
C₂₀H₂₁NO₆*C₃₆H₆₀O₃₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.67%	In ethanol; water at 25℃; for 72h; Darkness;	2.3. Preparation of DALY/a-CD inclusion complex The inclusion complex was prepared using the suspensionmethod. DALY (0.02 mmol, 7.1 mg) and a-CD (0.01 mmol, 9.7 mg)were dissolved in 5mL solution (ethanol andwater, V: V 1:5), andthe resulting suspension was magnetically stirred at 25 C for 3days in dark place. Afterwards, the 0.45 mm pore size nylon membranesyringe filter was used to remove the uncomplexed DALYresidue. The filtrate was then evaporated under reduced pressureand dried in vacuum to acquire DALY/a-CD inclusion complex asthe final product (yields: 64.67%).

Reference： [1]Feng, Xue-Pu; Na, Xin; Guo, Ya-Fei; Qian, Rui; Zhang, Jian-Qiang; Chen, Zhen; Yang, Rui [Journal of Molecular Structure, 2019, vol. 1181, p. 467 - 473]

83
[ 6493-05-6 ]
[ 10016-20-3 ]
C₁₃H₁₈N₄O₃*C₃₆H₆₀O₃₀ [ No CAS ]

Reference： [1]Zeitschrift fur Physikalische Chemie,2019,vol. 233,p. 1109 - 1127

84
[ 6138-41-6 ]
[ 10016-20-3 ]
C₇H₈NO₂⁽¹⁺⁾*Cl^(1-)*C₃₆H₆₀O₃₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In water; at 49.84 - 54.84℃; for 36.0h;	Both of the solid ICs (TgCl+alpha-CyD and TgCl+beta-CyD) were prepared in 1:1M ratios of TgCl and CyD. For each complex, 5.0mM of TgCl and 5.0mM of CyD were separately prepared in 10mL of water each and stirred for 4h. Then, the aqueous solution of TgCl was added dropwise to the aqueous solution of CyD. The resulting mixture was then stirred for 36hat 323-328K and filtered at this temperature. The mixture was then cooled to 278K and held at this temperature for 12h. The resulting solution was filtered to obtain a white powder, which was washed with water and ethanol respectively and dried in air. The yields of the solid inclusion complexes were 86% and 88% for TgCl+alpha-CyD and TgCl+beta-CyD respectively.

Reference： [1]Journal of Molecular Structure,2020,vol. 1200

85
[ 67-03-8 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₂H₁₇N₄OS⁽¹⁺⁾*Cl^(1-)*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. phosphate buffer; at 24.99℃; for 36h;pH 7.4;Thermodynamic data;	General procedure: Solubility of all the required compounds was specifically checked in triply distilled and de-ionized water. Mettler Toledo AG-285 having uncertainty±0.0003g was used to prepare all the solutions of THC, HSA, alpha-and beta-CD by mass at room temperature. All the stock solutions were prepared by mass dilution and freshly prepared solutions were used during each experiment in phosphate buffer aqueous solution of pH 7.4. Sufficient precautions had been taken during measuring weights, preparing solutions and performing all the respective experiments. Two solid ICs, THC+ alpha-CD and THC+beta-CD had been prepared in 1:1M ratio of THC and CD. 1.0mM of alpha-and beta-CD were each separately mixed with water and stirred for 4h. After that the aqueous solution of 1.0mM of THC was added dropwise to the respective solutions of CD and left for stirring near about 36h at 50-55C to prepare the corresponding two ICs. Just after filtration of the hot solutions, it is allowed to cool down to 5C and kept for 12h without any disturbing. The obtained suspension was then filtered and washed with ethanol and dried in air to get white polycrystalline powder.

Reference： [1]Journal of Molecular Liquids,2020,vol. 298

86
[ 50-63-5 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₈H₂₆ClN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 40 - 45℃; for 96.0h;Thermodynamic data;	General procedure: ICs (alpha-CD + CDP and beta-CD + CDP) were also preparedin the solid state taking 1:1 mol ratio of the drug CDP andeach CD. For this purpose 1.0 mmol CD was dissolved in20 mL water and 1.0 mmol drug CDP was dissolved in20 mL water. These two solutions are allowed to stir separatelyin a magnetic stirrer for 3 h. The aqueous solution ofthe drug was added dropwise into the aqueous solution ofthe cyclodextrin. Then the mixture is constantly stirred for4 days at 40-45 C. The solution was filtered at that temperature,then cooled to 5 C and kept for 24 h. The resultingsuspension was filtered and the white polycrystalline powderwas found, it was dried in air.

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2020,vol. 97,p. 65 - 76

87
[ 23828-92-4 ]
[ 10016-20-3 ]
C₃₆H₆₀O₃₀*C₁₃H₁₈Br₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 49.99℃;	To prepare 1:1 a solid Inclusion Complex between AmbroxolHydrochloride and alphaCD as well as with betaCD, at first, 30 mg of solidguest compound of AMB (which is also pretty much soluble in hotwater) was taken in a beaker and amount 40 ml of distilled water was added to it and placing it in a thermostated water bath at temperatureset at 323.15 K with constant stirring in a magnetic stirrer. Next, accuratelymeasured 70.39 mg of alphaCD and 82.13 mg of betaCD were addedin solid form in two different beakers slowly in presence of the constantstirring. It was kept in the thermostated water bath for 24-48 h.Thereafter, it was collected and dried in a hot oven & after that inclusioncomplexes in the solid form were obtained.

Reference： [1]Chemical Physics Letters,2020,vol. 748

88
[ 105542-98-1 ]
[ 10016-20-3 ]
2C₃₆H₆₀O₃₀*C₅H₆I₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 2578 - 2582
Angew. Chem.,2021,vol. 133,p. 2610 - 2614,5

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	10016-20-3	MDL No. :	MFCD00078207
Formula :	C₃₆H₆₀O₃₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFHDHCJBZVLPGP-RWMJIURBSA-N
M.W :	972.84	Pubchem ID :	444913
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P233	Keep container tightly closed.
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 10016-20-3 ] {[proInfo.proName]}

Quality Control of [ 10016-20-3 ]

Related Doc. of [ 10016-20-3 ]

Product Details of [ 10016-20-3 ]

Safety of [ 10016-20-3 ]

Application In Synthesis of [ 10016-20-3 ]

[ 10016-20-3 ] Synthesis Path-Upstream 1~3

[ 10016-20-3 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry