(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

Base Information

Chemical Name:(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol
CAS No.:1256362-36-3
Molecular Formula:C₂₁H₂₄O₅SSi
Molecular Weight:416.57
Hs Code.:

Synonyms:(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

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Chemical Property of (1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

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Technology Process of (1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

There total 1 articles about (1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol 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: 56.0%

: 1256362-35-2
(3S,6R)-3,6-dihydro-6-(2-((Z)-2-(dimethylphenyl)silyl)-2-(phenylthio)vinyl)-2H-pyran-3-ol

: 1256362-36-3
(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ol102383g

Reference yield: 91.0%

: 1256362-36-3
(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

: 917-54-4
methyllithium

: 1256362-37-4
(1R,2R,5S,6S)-5-((S)-1-(phenylsulfonyl)propan-2-yl)-4,7-dioxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: (1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol; methyllithium; With lithium bromide; trimethylsilylacetylene; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; at 34 ℃; for 1h; diastereoselective reaction;
DOI:10.1021/ol102383g

Reference yield: 80.0%

: 1256362-36-3
(1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol

: 1066-54-2
trimethylsilylacetylene

: 1256362-40-9
(1R,2R,5S,6S)-5-((S)-1-(phenylsulfonyl)but-3-yn-2-yl)-4,7-dioxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: (1R,2R,5S,6S)-5-((Z)-2-(dimethylphenyl)silyl)-2-(phenylsulfonyl)vinyl-4,7-dioxabicyclo[4.1.0]heptan-2-ol; trimethylsilylacetylene; With methyllithium; sodium bromide; lithium bromide; In diethyl ether; hexane; at -40 ℃; for 2.5h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; at 34 ℃; for 1h; diastereoselective reaction;
DOI:10.1021/ol102383g