Cholesteryl glucoside

Base Information

• Chemical Name: Cholesteryl glucoside
• CAS No.: 7073-61-2
• Molecular Formula: C33H54O7
• Molecular Weight: 562.77766
• DSSTox Substance ID: DTXSID50331472
• Nikkaji Number: J438.820H
• Wikidata: Q27102427
• Metabolomics Workbench ID: 50937
• ChEMBL ID: CHEMBL1170856
• Mol file: 7073-61-2.mol

Synonyms:cholesterol glucoside;cholesteryl D-glucopyranoside;cholesteryl glucoside;cholesteryl glucoside, (alpha-D)-isomer;cholesteryl glucoside, (beta-D)-isomer

Chemical Property of Cholesteryl glucoside

Chemical Property:

• PSA: 99.38000
• LogP: 5.21290
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 548.40768950
• Heavy Atom Count: 39
• Complexity: 874

Purity/Quality:

≥95% ^*data from raw suppliers

Cholesterol β-D-glucoside ≥97% (TLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C

Technology Process of Cholesteryl glucoside

There total 16 articles about Cholesteryl glucoside 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: 99.0%

(3β)-cholest-5-en-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6907-84-2) → cholesteryl β-D-glucopyranoside (7073-61-2)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

Reference yield: 90.0%

cholesterol (57-88-5) + 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) → cholesteryl β-D-glucopyranoside (7073-61-2)

Guidance literature:

cholesterol; 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate; With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 0.25h;

With sodium methylate;

DOI:10.1021/jo990603x

Reference yield: 90.0%

→ cholesteryl β-D-glucopyranoside (7073-61-2)

Guidance literature:

With methanol; sodium methylate; In dichloromethane; at 20 ℃; for 6h;

upstream raw materials:

(3β)-cholest-5-en-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

(5-Cholesten-3β-yl)-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosid

cholesterol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Refernces

• 1、 Higashi, Tatsuya,Horie, Yukiko,Ikegawa, Shigeo,Itoh, Mari,Jin, Shigeki,Murai, Tsuyoshi. "Analysis of steryl glucosides in rice bran-based fermented food by LC/ESI-MS/MS". . . Retrieved 2020.
• 2、 Davis, Ryan A.,Fettinger, James C.,Gervay-Hague, Jacquelyn. "Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-o-tetradecanoyl-α- d -cholesterylglycosides". . p. 8447 - 8452. Retrieved 2014.
• 3、 -. "Novel steroid -based amphiphiles and uses thereof". Paragraph 0165; 0170-0171; 0173; 0185-0187; 0223-0225. . Retrieved 2020/05/23.