7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester

Base Information

• Chemical Name: 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester
• CAS No.: 99223-27-5
• Molecular Formula: C₃₄H₆₄O₅SSi₂
• Molecular Weight: 641.116

Synonyms:7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester

Chemical Property of 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester

Chemical Property:

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Technology Process of 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester

There total 5 articles about 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic 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:

methyl 7-mercaptoheptanoate (99223-15-1) → 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester (99223-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / triethylamine / methanol

2: 1.) 2.0 M tert-BuLi, phenylthiocopper, (Me₂N)3P / 1.) pentane, ether; 2.) pentane, THF, ether

With tert.-butyl lithium; copper(I) thiophenolate; triethylamine; Hexamethylphosphorous triamide; In methanol;

DOI:10.1248/cpb.33.2359

Reference yield:

(4R)-tert-butyldimethylsilyloxy-2,3-epoxycyclopentanone (438527-27-6) → 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester (99223-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / triethylamine / methanol

2: 1.) 2.0 M tert-BuLi, phenylthiocopper, (Me₂N)3P / 1.) pentane, ether; 2.) pentane, THF, ether

With tert.-butyl lithium; copper(I) thiophenolate; triethylamine; Hexamethylphosphorous triamide; In methanol;

DOI:10.1248/cpb.33.2359

Reference yield:

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene (71399-48-9) → 7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-heptanoic acid methyl ester (99223-27-5)

Guidance literature:

Multi-step reaction with 3 steps

2: 99 percent

3: 1.) 2.0 M tert-BuLi, phenylthiocopper, (Me₂N)3P / 1.) pentane, ether; 2.) pentane, THF, ether

With tert.-butyl lithium; copper(I) thiophenolate; Hexamethylphosphorous triamide;

DOI:10.1248/cpb.33.2359

upstream raw materials:

4(R)-t-butyldimethylsilyloxy-2-(6-methoxycarbonylhexylthio)-2-cyclopentenone

(1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene

methyl 7-mercaptoheptanoate

Downstream raw materials:

7-[(2S,3R)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-heptanoic acid methyl ester

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