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

Base Information

Chemical Name:(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one
CAS No.:1355670-46-0
Molecular Formula:C₃₃H₅₀O₄Si₂
Molecular Weight:566.929
Hs Code.:

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

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

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

There total 5 articles about (1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one 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: 95.0%

: 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

: 1355670-46-0
(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one

Guidance literature:: (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; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

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

: 1355670-46-0
(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 1 h / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
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

: 1355670-46-0
(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-one

Guidance literature:: Multi-step reaction with 3 steps

2.1: 1H-imidazole / dichloromethane / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 1 h / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1016/j.tet.2011.11.052