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

Base Information

• Chemical Name: 5-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-pentanoic acid methyl ester
• CAS No.: 88462-20-8
• Molecular Formula: C₃₂H₆₀O₅SSi₂
• Molecular Weight: 613.062

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

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

Chemical Property:

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

There total 5 articles about 5-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-pentanoic 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 5-mercaptopentanoate (83009-94-3) → 5-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-pentanoic acid methyl ester (88462-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 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) → 5-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-pentanoic acid methyl ester (88462-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 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) → 5-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-pentanoic acid methyl ester (88462-20-8)

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:

5-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enylsulfanyl]-pentanoic acid methyl ester

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

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

methyl 5-mercaptopentanoate

Downstream raw materials:

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

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