benzyl 3α,7α-dihydroxy-5β-cholan-24-oate

Base Information

• Chemical Name: benzyl 3α,7α-dihydroxy-5β-cholan-24-oate
• CAS No.: 111992-94-0
• Molecular Formula: C₃₁H₄₆O₄
• Molecular Weight: 482.704
• Mol file: 111992-94-0.mol

Synonyms:benzyl 3α,7α-dihydroxy-5β-cholan-24-oate

Chemical Property of benzyl 3α,7α-dihydroxy-5β-cholan-24-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3α,7α-dihydroxy-5β-cholan-24-oate

There total 1 articles about benzyl 3α,7α-dihydroxy-5β-cholan-24-oate 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: 92.0%

chenodeoxycholic acid (474-25-9) + benzyl bromide (100-39-0) → benzyl 3α,7α-dihydroxy-5β-cholan-24-oate (111992-94-0)

Guidance literature:

With caesium carbonate; In acetonitrile; Reflux;

Reference yield: 79.0%

benzyl 3α,7α-dihydroxy-5β-cholan-24-oate (111992-94-0) + chloro-trimethyl-silane (75-77-4) → C37H62O4Si2

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 5 ℃;

Reference yield: 69.0%

benzyl 3α,7α-dihydroxy-5β-cholan-24-oate (111992-94-0) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → benzyl 3α,7α-dihydroxy-5β-cholan-24-oate-3-β-D-glucuronide methyl ester triacetate

Guidance literature:

With Fetizon’s reagent; In toluene; at 38 ℃; under 5171.62 Torr; regioselective reaction; Molecular sieve; Flow reactor;

DOI:10.1039/c4ob01911c

upstream raw materials:

chenodeoxycholic acid

benzyl bromide

Downstream raw materials:

Pyrene-1-carboxylic acid (3R,5R,7R,8R,9S,10S,13R,14S,17R)-17-((R)-3-benzyloxycarbonyl-1-methyl-propyl)-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Pyrene-1-carboxylic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-((R)-3-benzyloxycarbonyl-1-methyl-propyl)-7-(2-chloro-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Pyrene-1-carboxylic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-((R)-3-benzyloxycarbonyl-1-methyl-propyl)-10,13-dimethyl-7-(2-1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl-acetoxy)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Pyrene-1-carboxylic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-((R)-3-benzyloxycarbonyl-1-methyl-propyl)-10,13-dimethyl-7-(2-1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl-acetoxy)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Refernces

• 1、 Mostarda, Serena,Passeri, Daniela,Carotti, Andrea,Cerra, Bruno,Colliva, Carolina,Benicchi, Tiziana,Macchiarulo, Antonio,Pellicciari, Roberto,Gioiello, Antimo. "Synthesis, physicochemical properties, and biological activity of bile acids 3-glucuronides: Novel insights into bile acid signalling and detoxification". . p. 349 - 358. Retrieved 2017/12/28.
• 2、 Mostarda, Serena,Filipponi, Paolo,Sardella, Roccaldo,Venturoni, Francesco,Natalini, Benedetto,Pellicciari, Roberto,Gioiello, Antimo. "Glucuronidation of bile acids under flow conditions: Design of experiments and Koenigs-Knorr reaction optimization". . p. 9592 - 9600. Retrieved 2015/02/19.