cholestane-2,3-diol

Base Information

• Chemical Name: cholestane-2,3-diol
• CAS No.: 10146-89-1
• Molecular Formula: C₂₇H₄₈O₂
• Molecular Weight: 404.677
• Mol file: 10146-89-1.mol

Synonyms:5a-Cholestane-2b,3b-diol (8CI); 2b,3b-Dihydroxy-5a-cholestane;NSC 117602

Chemical Property of cholestane-2,3-diol

Chemical Property:

• Vapor Pressure: 1.33E-11mmHg at 25°C
• Boiling Point: 488.8°Cat760mmHg
• Flash Point: 199.6°C
• Density: 1.003g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cholestane-2,3-diol

There total 40 articles about cholestane-2,3-diol 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: 98.0%

Cholestano-<2α,3α-d>-dioxol-2'-on (80235-45-6,81163-55-5) → Cholestan-2α,3α-diol (10146-89-1,16126-30-0,16126-32-2,16991-05-2,20312-09-8,25494-76-2,57377-69-2,111822-10-7)

Guidance literature:

With potassium carbonate; In methanol; water; for 5h; Heating;

Reference yield: 87.0%

cholest-2-ene (13901-19-4,15910-23-3,570-73-0) → 5α-cholestane-2β, 3β-diol (10146-89-1)

Guidance literature:

cholest-2-ene; With ammonium cerium(IV) nitrate; iodine; acetic acid; for 10h; Heating;

With potassium hydroxide; In methanol; for 0.5h; Heating;

DOI:10.1055/s-2005-916040

Reference yield: 85.0%

2α,3α-epoxy-5α-cholestane (1753-61-3) → (2β-3α-5α)-cholestane-2,3-diol (16126-32-2,10146-89-1,16126-30-0,16991-05-2,20312-09-8,25494-76-2,57377-69-2,111822-10-7)

Guidance literature:

With periodic acid; In water; acetone; Heating;

DOI:10.1016/j.tet.2005.01.104

upstream raw materials:

Acetic acid (2S,3S,5S,10S,13R,17R)-17-(1,5-dimethyl-hexyl)-2-iodo-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

5α-Cholest-2-ene

Acetic acid (2R,3S,5S,10S,13R,17R)-17-(1,5-dimethyl-hexyl)-2-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Acetic acid (2R,3S,5S,10S,13R,17R)-3-acetoxy-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester

Downstream raw materials:

2,3-seco-5α-cholestane-2,3-dicarboxylic acid

3β-(toluene-4-sulfonyloxy)-5α-cholestan-2β-ol

Refernces

• 1、 Sepe, Valentina,Ummarino, Raffaella,D'Auria, Maria Valeria,Lauro, Gianluigi,Bifulco, Giuseppe,D'Amore, Claudio,Renga, Barbara,Fiorucci, Stefano,Zampella, Angela. "Modification in the side chain of solomonsterol A: Discovery of cholestan disulfate as a potent pregnane-X-receptor agonist". . p. 6350 - 6362. Retrieved 2012.
• 2、 Georg. "". . p. 114. Retrieved 1954.
• 3、 Horiuchi, C. Akira,Satoh, J. Yasuo. "Syntheses of Steroidal trans-Iodo Acetates". . p. 426 - 428. Retrieved 1987.
• 4、 Henbest,Smith. "-". . p. 926. Retrieved 1957.
• 5、 Horiuchi, C. Akira,Dan, Gong,Sakamoto, Masaki,Suda, Kazuhiko,Usui, Shigeru,Sakamoto, Okihiko,Kitoh, Shinya,Watanabe, Satoshi,Utsukihara, Takamitsu,Nozaki, Sukekatsu. "A new synthesis of cis-diol from alkene using iodine-ammonium cerium(IV) nitrate". . p. 2861 - 2864. Retrieved 2005.
• 6、 Marker,Rohrmann. "". . p. 3314,3316. Retrieved 1939.