(3β)-3-(tert-ButyldiMethylsilyl)oxy-chol-5-en-24-oic Acid Methyl Ester

Base Information

• Chemical Name: (3β)-3-(tert-ButyldiMethylsilyl)oxy-chol-5-en-24-oic Acid Methyl Ester
• CAS No.: 114011-35-7
• Molecular Formula: C₃₁H₅₄O₃Si
• Molecular Weight: 502.853
• Mol file: 114011-35-7.mol

Synonyms:3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester

Chemical Property of (3β)-3-(tert-ButyldiMethylsilyl)oxy-chol-5-en-24-oic Acid Methyl Ester

Chemical Property:

• Melting Point: 157-160oC
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

(3β)-3-(tert-Butyldimethylsilyl)oxy-chol-5-en-24-oicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3β)-3-(tert-Butyldimethylsilyl)oxy-chol-5-en-24-oic Acid Methyl Ester is an intermediate in the preparation of steroidal antitumor compounds.

Technology Process of (3β)-3-(tert-ButyldiMethylsilyl)oxy-chol-5-en-24-oic Acid Methyl Ester

There total 16 articles about (3β)-3-(tert-ButyldiMethylsilyl)oxy-chol-5-en-24-oic Acid 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: 99.0%

methanol (67-56-1) + 3β-hydroxy-5-cholenoic acid (5255-17-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester (114011-35-7)

Guidance literature:

methanol; 3β-hydroxy-5-cholenoic acid; With toluene-4-sulfonic acid; at 60 ℃;

tert-butyldimethylsilyl chloride; With 1H-imidazole; dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield: 97.0%

methyl 5-cholenoate (20231-57-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester (114011-35-7)

Guidance literature:

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2015.03.053

Reference yield: 93.0%

methyl (22E)-3β-(tert-butyldimethylsilyloxy)chol-5,22-dien-24-oate (164298-05-9) → 3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester (114011-35-7)

Guidance literature:

With magnesium; In methanol; benzene; at 25 ℃;

DOI:10.1016/S0040-4039(98)02181-9

upstream raw materials:

methyl 5-cholenoate

tert-butyldimethylsilyl chloride

methyl (22E)-3β-(tert-butyldimethylsilyloxy)chol-5,22-dien-24-oate

(2β,20S)-3-<(tert-butyldimethylsilyl)oxy>pregn-5-ene-20-carboxaldehyde

Downstream raw materials:

demosterol

tert-Butyl-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-dimethyl-silane

(24S)-24,25-epoxycholesterol

24(R),25-Epoxycholesterol

Refernces

• 1、 Dubowchik, Gene M.,Firestone, Raymond A.. "The synthesis of branched steroidal prodrugs of nitrogen mustard for antitumor targeting via reconstituted LDL". . p. 4523 - 4526. Retrieved 1994.
• 2、 Zhao, Fei,Wu, Yiran,Zhou, Fang,Xue, Dongxiang,Zhao, Simeng,Lu, Wanglong,Liu, Xiaoyan,Hu, Tao,Qiu, Yanli,Li, Rongyan,Gu, Tangjie,Xu, Yueming,Xu, Fei,Zhong, Guisheng,Jiang, Zhongxing,Zhao, Suwen,Tao, Houchao. "Elucidation of Distinct Modular Assemblies of Smoothened Receptor by Bitopic Ligand Measurement". supporting information. p. 13830 - 13840. Retrieved 2021/09/28.
• 3、 -. "Cholesterol molecular probe as well as preparation method and application thereof". Paragraph 0119; 0120. . Retrieved 2017/07/21.