(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

Base Information

Chemical Name:(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol
CAS No.:1355670-44-8
Molecular Formula:C₃₃H₅₂O₄Si₂
Molecular Weight:568.944
Hs Code.:

Synonyms:(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

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Chemical Property of (1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

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Technology Process of (1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

There total 4 articles about (1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-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: 86.0%

: 915694-39-2
(+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1355670-44-8
(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; regioselective reaction;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 915694-38-1
(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

: 1355670-44-8
(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

2: 1H-imidazole / dichloromethane / 0 - 20 °C

With 1H-imidazole; In dichloromethane;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 303963-93-1
(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

: 1355670-44-8
(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: diethylzinc

3: 1H-imidazole / dichloromethane / 0 - 20 °C

With 1H-imidazole; diethylzinc; In dichloromethane; 1: Simmons-Smith reaction;
DOI:10.1016/j.tet.2011.11.052