[(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane
CAS No.:117653-58-4
Molecular Formula:C₂₆H₄₂O₆SSi
Molecular Weight:510.767
Hs Code.:

[(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

There total 12 articles about [(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane 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: 61.0%

: 117653-57-3,117708-34-6
tert-Butyl-[(1S,4R,5S)-2,3-dimethyl-5-phenylsulfanylmethyl-4-(tetrahydro-pyran-2-yloxymethyl)-cyclopent-2-enyloxy]-dimethyl-silane

: 117653-58-4,117708-28-8,117708-35-7,117708-36-8
[(1R,2R,3R,4R,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

: 117653-58-4,117708-28-8,117708-35-7,117708-36-8
[(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 - -5 ℃; for 3.5h;
DOI:10.1021/jo00262a017

Reference yield: 61.0%

: 117653-57-3,117708-34-6
tert-Butyl-[(1S,4R,5S)-2,3-dimethyl-5-phenylsulfanylmethyl-4-(tetrahydro-pyran-2-yloxymethyl)-cyclopent-2-enyloxy]-dimethyl-silane

: 117653-58-4,117708-28-8,117708-35-7,117708-36-8
[(1R,2R,3R,4R,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

: 117653-58-4,117708-28-8,117708-35-7,117708-36-8
[(1R,2S,3S,4S,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 - -5 ℃; for 3.5h;
DOI:10.1021/jo00262a017

Reference yield:

: 162340-83-2
2,3-Dimethyl-5-methylene-4-<<(tetrahydropyran-2-yl)oxy>methyl>-2-cyclopenten-1-one

: 117653-58-4,117708-28-8,117708-35-7,117708-36-8
[(1R,2R,3R,4R,5S)-3-Benzenesulfonylmethyl-1,5-dimethyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-oxa-bicyclo[3.1.0]hex-2-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / triethylamine / tetrahydrofuran / 1.75 h / 0 - 25 °C

2: 89 percent / n-butyllithium, DIBAL / tetrahydrofuran / 0.5 h / -78 °C

3: 88 percent / imidazole / dimethylformamide / 5 h / 25 °C

4: 15 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 3.5 h / -20 - -5 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00262a017