(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

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Chemical Name:(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol
CAS No.:139277-12-6
Molecular Formula:C₂₅H₄₄O₅SSi₂
Molecular Weight:512.858
Hs Code.:

Synonyms:(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

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Chemical Property of (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

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Technology Process of (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

There total 7 articles about (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol 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: 80.0%

: 139277-10-4
(1S,2S,3S,4R,5R)-2-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]heptane

: 139277-12-6
(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

Guidance literature:: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In toluene; at -78 ℃; for 2h;
DOI:10.1021/jo00033a002

Reference yield:

: 24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2
(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

: 139277-12-6
(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / CHCl₃ / 48 h / 0 deg C to r.t.

2: 90 percent / LAH / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

4: 95 percent / magnesium monoperoxyphthalate (MMPP) / methanol / 0 °C

5: 80 percent / n-BuLi, TMEDA / toluene / 2 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00033a002

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139277-12-6
(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 95 percent / magnesium monoperoxyphthalate (MMPP) / methanol / 0 °C

3: 80 percent / n-BuLi, TMEDA / toluene / 2 h / -78 °C

With 1H-imidazole; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; magnesium monoperoxyphthalate hexahydrate; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00033a002