(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

Base Information

Chemical Name:(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene
CAS No.:77493-68-6
Molecular Formula:C₁₈H₂₈O₆S₂Si
Molecular Weight:432.634
Hs Code.:

Synonyms:(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

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Chemical Property of (1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

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Technology Process of (1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

There total 9 articles about (1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-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: 91.0%

: 812-01-1
methyl chlorosulfate

: 77493-67-5
(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-hydroxy-2-(phenylsulfonyl)-2-cyclopentene

: 77493-68-6
(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo00161a010

Reference yield:

: 77520-13-9
(1R,2R)-trans-2-(Phenylsulfinyl)-3-cyclopenten-1-ol

: 77493-68-6
(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine hydrobromide / tetrahydrofuran / 18 h / Heating

2: 83 percent / aq. sodium hydroxide

3: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 6 h / 0 - 25 °C

4: 1.) DBU, 2.) (C₂H₅)3N, DMAP / 1.) CH₂Cl₂, 25 deg C, 0.5 h, 2.) 24 h

5: (C₂H₅)3N / CH₂Cl₂

With dmap; sodium hydroxide; Pyridine hydrobromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00398a049

Reference yield:

: 77520-12-8
(1R,2R)-2-Phenylsulfanyl-cyclopent-3-enol

: 77493-68-6
(1R,4R)-trans-4-(tert-Butyldimethylsiloxy)-1-(methanesulfonoxy)-2-(phenylsulfonyl)-2-cyclopentene

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.25 h / -78 °C

2: pyridine hydrobromide / tetrahydrofuran / 18 h / Heating

3: 83 percent / aq. sodium hydroxide

4: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 6 h / 0 - 25 °C

5: 1.) DBU, 2.) (C₂H₅)3N, DMAP / 1.) CH₂Cl₂, 25 deg C, 0.5 h, 2.) 24 h

6: (C₂H₅)3N / CH₂Cl₂

With dmap; sodium hydroxide; Pyridine hydrobromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00398a049