MONO-6-O-(P-TOLUENESULFONYL)-GAMMA-CYCLODEXTRIN

Base Information

• Chemical Name: MONO-6-O-(P-TOLUENESULFONYL)-GAMMA-CYCLODEXTRIN
• CAS No.: 97227-33-3
• Molecular Formula: C55H86 O42 S
• Molecular Weight: 1451.33
• Nikkaji Number: J1.363.141G
• Mol file: 97227-33-3.mol

Synonyms:2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-Hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontane,g-cyclodextrin deriv.; 6-O-Tosyl-g-cyclodextrin;Mono-6-(p-tolylsulfonyl)-g-cyclodextrin; Mono-6-O-tosyl-g-cyclodextrin; g-Cyclodextrin 6-monotosylate

Chemical Property of MONO-6-O-(P-TOLUENESULFONYL)-GAMMA-CYCLODEXTRIN

Chemical Property:

• PSA: 664.72000
• LogP: -14.60400
• Solubility.: soluble in Dimethylformamide
• XLogP3: -15.1
• Hydrogen Bond Donor Count: 23
• Hydrogen Bond Acceptor Count: 42
• Rotatable Bond Count: 11
• Exact Mass: 1450.4314379
• Heavy Atom Count: 98
• Complexity: 2580

Purity/Quality:

98% ^*data from raw suppliers

Mono-6-O-(p-toluenesulfonyl)-γ-cyclodextrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C3C(C(C(O2)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(C(C7O)O)OC8C(OC(C(C8O)O)OC9C(OC(C(C9O)O)OC1C(OC(O3)C(C1O)O)CO)CO)CO)CO)CO)CO)CO)O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2[C@@H]3[C@@H]([C@H]([C@H](O2)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@@H]([C@@H]([C@H]8O)O)O[C@@H]9[C@H](O[C@@H]([C@@H]([C@H]9O)O)O[C@@H]1[C@H](O[C@H](O3)[C@@H]([C@H]1O)O)CO)CO)CO)CO)CO)CO)CO)O)O
• Uses: Mono-6-O-(p-toluenesulfonyl)-gamma-cyclodextrin (CAS# 97227-33-3) is a useful macromolecule used in the preparation of γ-cyclodextrin derivatives, some of which are able to retain permanent positive charges.

Technology Process of MONO-6-O-(P-TOLUENESULFONYL)-GAMMA-CYCLODEXTRIN

There total 2 articles about MONO-6-O-(P-TOLUENESULFONYL)-GAMMA-CYCLODEXTRIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.79%

p-toluenesulfonyl chloride (98-59-9) + cyclomaltooctaose (17465-86-0) → 6I-O-p-toluenesulfonyl-γ-cyclodextrin (97227-33-3)

Guidance literature:

In pyridine; for 1h;

DOI:10.1246/cl.1988.1329

Reference yield: 7.5%

p-toluenesulfonyl chloride (98-59-9) + cyclomaltooctaose (17465-86-0) → 6I-O-p-toluenesulfonyl-γ-cyclodextrin (97227-33-3) + 2I-O-(p-toluenesulfonyl)-γ-cyclodextrin (97227-32-2)

Guidance literature:

cyclomaltooctaose; With di(n-butyl)tin oxide; In N,N-dimethyl-formamide; at 100 ℃; for 2h; Inert atmosphere;

p-toluenesulfonyl chloride; With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2010.02.005

Reference yield: 99.4%

6I-O-p-toluenesulfonyl-γ-cyclodextrin (97227-33-3) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-((2R,3S,4R,5R)-4,5,6-trihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

With acetate buffer; Taka amylase A; calcium chloride; In water; at 10 ℃; for 48h;

DOI:10.1246/bcsj.62.3150

upstream raw materials:

p-toluenesulfonyl chloride

cyclomaltooctaose

Refernces

• 1、 Fujita, Kahee,Tahara, Tsutomu,Imoto, Taiji,Koga, Toshitaka. "Enzymatic Preparation of Specifically Modified Linear Maltooligosaccharides through Taka-amylase A-catalyzed Hydrolysis of 6-O-Arenesulfonyl-γ-cyclodextrins". . p. 1329 - 1332. Retrieved 1988.
• 2、 Fujita,Tahara,Koga,Imoto. "Enzymatic synthesis of specifically modified linear oligosaccharides from γ-cyclodextrin derivatives. Study on importance of active sites of Taka amylase A.". . p. 3150 - 3154. Retrieved 1989.
• 3、 Rao, Ming,Kanagaraj, Kuppusamy,Fan, Chunying,Ji, Jiecheng,Xiao, Chao,Wei, Xueqin,Wu, Wanhua,Yang, Cheng. "Photocatalytic Supramolecular Enantiodifferentiating Dimerization of 2-Anthracenecarboxylic Acid through Triplet-Triplet Annihilation". supporting information. p. 1680 - 1683. Retrieved 2018/03/23.
• 4、 Van Guyse, Joachim F. R.,de la Rosa, Victor R.,Hoogenboom, Richard. "Mechanochemical Preparation of Stable Sub-100 nm γ-Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization". . p. 2758 - 2766. Retrieved 2018/02/06.