Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)-

Base Information

• Chemical Name: Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)-
• CAS No.: 301695-61-4
• Molecular Formula: C27H46O3
• Molecular Weight: 418.66
• DSSTox Substance ID: DTXSID00409418
• Metabolomics Workbench ID: 198764
• Nikkaji Number: J1.437.052H
• Wikidata: Q82215246
• Mol file: 301695-61-4.mol

Synonyms:301695-61-4;Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)-;(5S,7R,8R,9S,10S,13R,14S,17R)-7-Hydroxy-17-((2R,5R)-5-hydroxy-6-methylheptan-2-yl)-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one;(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one;(5alpha,7alpha,24R)-7,24-Dihydroxycholestan-3-one;(5-alpha,7-alpha,24R)-7,24-dihydroxycholestan-3-one;SCHEMBL3297129;DTXSID00409418;BMA69561;CS-M3655;AKOS027384075;CS-15145;(5,7,24R)-7,24-Dihydroxycholestan-3-one;C13098;(5|A,7|A,24R)-7,24-Dihydroxycholestan-3-one;(5+/-,7+/-,24R)-7,24-Dihydroxycholestan-3-one

Chemical Property of Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)-

Chemical Property:

• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 418.34469533
• Heavy Atom Count: 30
• Complexity: 644

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCC3C2C(CC4C3(CCC(=O)C4)C)O)C)O
• Isomeric SMILES: C[C@H](CC[C@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@@H]4[C@@]3(CCC(=O)C4)C)O)C

Technology Process of Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)-

There total 46 articles about Cholestan-3-one, 7,24-dihydroxy-, (5a,7a,24R)- 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: 96.0%

(5α,7α,24R)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one (610313-92-3) → (5α,7α,24R)-7,24-dihydroxy-3-ketocholestane (301695-61-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; Heating;

DOI:10.1021/ol035062j

Reference yield: 92.0%

7α-methoxymethyl-3-(ethane-1',2'-diyldioxy)-5α-24R-hydroxycholestane (500224-95-3) → (5α,7α,24R)-7,24-dihydroxy-3-ketocholestane (301695-61-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; Heating;

DOI:10.1016/S0040-4039(01)00191-5

Reference yield: 89.0%

(5α,7α,24R)-7,24-dihydroxy-3-dioxolane-cholestane (301695-59-0) → (5α,7α,24R)-7,24-dihydroxy-3-ketocholestane (301695-61-4)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 4h;

DOI:10.1021/ol0059495

upstream raw materials:

(5α,7α,24R)-7,24-dihydroxy-3-dioxolane-cholestane

7α-methoxymethyl-3-(ethane-1',2'-diyldioxy)-5α-24R-hydroxycholestane

(5α,7α,24R)-24-hydroxy-7-(methoxymethoxy)cholestan-3-one

(5α,24R)-24-benzoyloxy-7α-hydroxycholestan-3-one

Refernces

• 1、 Zhou, Xiang-Dong,Cai, Feng,Zhou, Wei-Shan. "A new highly stereoselective construction of the sidechain of squalamine through improved Sharpless catalytic asymmetric dihydroxylation". . p. 2537 - 2539. Retrieved 2001.
• 2、 Kinney, William A.,Zhang, Xuehai,Williams, Jon I.,Johnston, Sean,Michalak, Ronald S.,Deshpande, Milind,Dostal, Larry,Rosazza, John P. N.. "A short formal synthesis of squalamine from a microbial metabolite". . p. 2921 - 2922. Retrieved 2000.
• 3、 Okumura, Kazuo,Nakamura, Yutaka,Takeuchi, Seiji,Kato, Isao,Fujimoto, Yoshinori,Ikekawa, Nobuo. "Formal synthesis of squalamine from desmosterol". . p. 1177 - 1182. Retrieved 2007/10/03.