5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester

Base Information

• Chemical Name: 5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester
• CAS No.: 27240-83-1
• Molecular Formula: C27H44 O5
• Molecular Weight: 448.643
• DSSTox Substance ID: DTXSID00585100
• Mol file: 27240-83-1.mol

Synonyms:5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester;Methyl 3alpha-acetoxy-12alpha-hydroxycholanate;DTXSID00585100;NCGC00485026-01;B-PIPERIDINOPROPIONALDEHYDEDIMETHYLACETAL;J-016704;5 beta -Cholanic acid-3 alpha ,12 alpha -diol 3-acetate methyl ester;METHYL 3-ALPHA-ACETOXY-12-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OATE;Methyl (3alpha,8xi,9xi,10xi,12alpha,13xi,14xi,17xi)-3-(acetyloxy)-12-hydroxycholan-24-oate

Chemical Property of 5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester

Chemical Property:

• Vapor Pressure: 6.19E-13mmHg at 25°C
• Refractive Index: 1.525
• Boiling Point: 518.9°C at 760 mmHg
• Flash Point: 161°C
• PSA: 72.83000
• Density: 1.1g/cm³
• LogP: 5.13710
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 448.31887450
• Heavy Atom Count: 32
• Complexity: 721

Purity/Quality:

98%,99%, ^*data from raw suppliers

5β-Cholanic acid-3α,12α-diol 3-acetate methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)OC(=O)C)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)C1CCC2C1([C@H](CC3C2CCC4C3(CC[C@H](C4)OC(=O)C)C)O)C

Technology Process of 5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester

There total 25 articles about 5beta-Cholanic acid-3alpha,12alpha-diol 3-acetate methyl ester 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: 99.6%

methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate (5143-55-5) → methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate (27240-83-1)

Guidance literature:

methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate; With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 - 10 ℃; for 5h;

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 5 ℃; Product distribution / selectivity;

Reference yield: 92.0%

methyl deoxycholate (3245-38-3) + acetic anhydride (108-24-7) → methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate (27240-83-1)

Guidance literature:

With pyridine; In benzene; at 20 ℃; for 12h; regioselective reaction;

DOI:10.1248/cpb.c16-00247

Reference yield: 90.0%

acetic acid methyl ester (79-20-9) + Deoxycholic acid (83-44-3) → methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate (27240-83-1)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(98)00463-8

upstream raw materials:

methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate

methyl deoxycholate

acetic anhydride

acetic acid methyl ester

Downstream raw materials:

12-oxolithocholic acid

(R)-methyl 4-((5R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Deoxycholic acid

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Refernces

• 1、 Popadyuk, Irina I.,Markov, Andrey V.,Salomatina, Oksana V.,Logashenko, Evgeniya B.,Shernyukov, Andrey V.,Zenkova, Marina A.,Salakhutdinov, Nariman F.. "Synthesis and biological activity of novel deoxycholic acid derivatives". . p. 5022 - 5034. Retrieved 2015.
• 2、 Koechlin,Reichstein. "-". . p. 918,927. Retrieved 1942.
• 3、 He, Xiao-Long,Xing, Yajing,Gu, Xiang-Zhong,Xiao, Jie-Xin,Wang, Ying-Ying,Yi, Zhengfang,Qiu, Wen-Wei. "The synthesis and antitumor activity of lithocholic acid and its derivatives". . p. 54 - 60. Retrieved 2017/08/02.
• 4、 -. "Synthesizing method of lithocholic acid". Paragraph 0048; 0049. . Retrieved 2016/12/22.