Chol-6-en-24-oic acid, 3,7-bis[(trimethylsilyl)oxy]-, phenylmethyl ester, (3α,5β)-

Base Information

• Chemical Name: Chol-6-en-24-oic acid, 3,7-bis[(trimethylsilyl)oxy]-, phenylmethyl ester, (3α,5β)-
• CAS No.: 1352328-65-4
• Molecular Formula: C₃₇H₆₀O₄Si₂
• Molecular Weight: 625.052
• Mol file: 1352328-65-4.mol

Synonyms:benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate

Chemical Property of Chol-6-en-24-oic acid, 3,7-bis[(trimethylsilyl)oxy]-, phenylmethyl ester, (3α,5β)-

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Phenylmethyl3,7-Bis[(trimethylsilyl)oxy]-chol-6-en-24-oicAcidEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenylmethyl 3,7-Bis[(trimethylsilyl)oxy]-chol-6-en-24-oic Acid Ester is an intermediate used in the synthesis of 6-Ethylchenodeoxycholic-d5 Acid (E899812), which is an isotope labelled compound of 6-Ethylchenodeoxycholic Acid (E899810), which is used in the investigative treatment of primary biliary cholangitis. Primary biliary cholangitis is an autoimmune disease of the liver that slowly progresses to cirrhosis.

Technology Process of Chol-6-en-24-oic acid, 3,7-bis[(trimethylsilyl)oxy]-, phenylmethyl ester, (3α,5β)-

There total 4 articles about Chol-6-en-24-oic acid, 3,7-bis[(trimethylsilyl)oxy]-, phenylmethyl ester, (3α,5β)- 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:

chloro-trimethyl-silane (75-77-4) + 3α-hydroxy-7-keto-5β-24-cholanic acid benzyl ester (1352328-64-3) → benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate (1352328-65-4)

Guidance literature:

chloro-trimethyl-silane; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.833333h; Inert atmosphere;

3α-hydroxy-7-keto-5β-24-cholanic acid benzyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 0.916667h; Inert atmosphere;

With triethylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm201004p

Reference yield:

chenodeoxycholic acid (474-25-9) → benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate (1352328-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutylammomium bromide; acetic acid; sodium bromide / methanol; water; ethyl acetate / 20 °C / Inert atmosphere

1.2: 6 h / 0 - 20 °C / Inert atmosphere

1.3: 0.08 h / 15 °C / Inert atmosphere

2.1: caesium carbonate / acetonitrile / 150 °C / Inert atmosphere

2.2: 24 h / Inert atmosphere; Reflux

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.83 h / -78 °C / Inert atmosphere

3.2: 0.92 h / -78 °C / Inert atmosphere

3.3: 1 h / -78 °C / Inert atmosphere

With n-butyllithium; tetrabutylammomium bromide; caesium carbonate; acetic acid; diisopropylamine; sodium bromide; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jm201004p

Reference yield:

7-Ketolithocholic acid (4651-67-6) → benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate (1352328-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: caesium carbonate / acetonitrile / 150 °C / Inert atmosphere

1.2: 24 h / Inert atmosphere; Reflux

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.83 h / -78 °C / Inert atmosphere

2.2: 0.92 h / -78 °C / Inert atmosphere

2.3: 1 h / -78 °C / Inert atmosphere

With n-butyllithium; caesium carbonate; diisopropylamine; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/jm201004p

upstream raw materials:

chloro-trimethyl-silane

3α-hydroxy-7-keto-5β-24-cholanic acid benzyl ester

chenodeoxycholic acid

7-Ketolithocholic acid

Downstream raw materials:

3α-hydroxy-6-ethylidene-7-oxo-5β-cholanoic acid benzyl ester

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR PREPARATION OF OBETICHOLIC ACID". Page/Page column 9; 10. . Retrieved 2019/01/05.
• 2、 Sepe, Valentina,Ummarino, Raffaella,Dauria, Maria Valeria,Chini, Maria Giovanna,Bifulco, Giuseppe,Renga, Barbara,Damore, Claudio,Debitus, Cécile,Fiorucci, Stefano,Zampella, Angela. "Conicasterol E, a small heterodimer partner sparing farnesoid X receptor modulator endowed with a pregnane X receptor agonistic activity, from the marine sponge Theonella swinhoei". experimental part. p. 84 - 93. Retrieved 2012/03/26.