6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

Base Information

• Chemical Name: 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester
• CAS No.: 83009-66-9
• Molecular Formula: C₃₃H₆₂O₅SSi₂
• Molecular Weight: 627.089

Synonyms:6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

Chemical Property of 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

Chemical Property:

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Technology Process of 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

There total 5 articles about 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic 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:

1-mercapto-5-carbomethoxy-pentane (20756-86-9) → 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83009-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / triethylamine / methanol / 3 h / Ambient temperature

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) → 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83009-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / triethylamine / methanol / 3 h / Ambient temperature

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) → 6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83009-66-9)

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:

methyl-6-<(4R)-tert-butyldimethylsilyloxy-2-oxo-5-cyclopenten-1-ylthio>hexanoate

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

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

1-mercapto-5-carbomethoxy-pentane

Downstream raw materials:

15-cyclohexyl-w-pentanor-7-thiaprostaglandin E₁ methyl ester

15-cyclohexyl-ω-pentanor-7-thiaprostaglandin E₁

6-[(1R,2S,3R)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentanesulfinyl]-hexanoic acid methyl ester

6-[(1R,2S,3R)-2-((R)-3-Cyclohexyl-3-hydroxy-propyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

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