(1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene

Base Information

• Chemical Name: (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene
• CAS No.: 85453-08-3
• Molecular Formula: C₂₃H₄₀O₄SSi₂
• Molecular Weight: 468.805

Synonyms:(1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene

Chemical Property of (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene

Chemical Property:

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Technology Process of (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene

There total 4 articles about (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene 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:

Dichloro-((1S,2S)-2-phenylsulfanyl-cyclopent-3-enyloxy)-silane (85453-06-1) → (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene (85453-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1: HF / H₂O

With hydrogen fluoride; In water;

DOI:10.1021/jo00161a010

Reference yield:

(1-Phenyl-ethyl)-carbamic acid (1S,2S)-2-phenylsulfanyl-cyclopent-3-enyl ester (85548-65-8,85453-05-0) → (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene (85453-08-3)

Guidance literature:

Multi-step reaction with 4 steps

1: HSiCl₃, Et₃N / toluene / 0 °C

2: HF / H₂O

With trichlorosilane; hydrogen fluoride; triethylamine; In water; toluene;

DOI:10.1021/jo00161a010

Reference yield:

trans-1-hydroxy-2-phenylthiocyclopent-3-ene (77520-17-3) → (1S,4R)-cis-1,4-Bis(tert-butyldimethylsiloxy)-2-(phenylsulfonyl)-2-cyclopentene (85453-08-3)

Guidance literature:

DOI:10.1021/jo00161a010

upstream raw materials:

(1S,2R,3R,4R)-cis-3,4-Epoxy-trans-2-(phenylsulfonyl)cyclopentan-1-ol

tert-butyldimethylsilyl chloride

trans-1-hydroxy-2-phenylthiocyclopent-3-ene

Dichloro-((1S,2S)-2-phenylsulfanyl-cyclopent-3-enyloxy)-silane

Downstream raw materials:

(1S,4R)-cis-1,4-Dihydroxy-2-(phenylsulfonyl)-2-cyclopentene

{(1S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopent-2-enesulfonyl}-benzene

{(4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopent-1-enesulfonyl}-benzene

C₂₀H₃₄NO₃SSi⁽¹⁺⁾*FO₃S^(1-)

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