(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

Base Information

Chemical Name:(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol
CAS No.:915694-42-7
Molecular Formula:C₄₄H₅₈O₄Si₂
Molecular Weight:707.113
Hs Code.:

Synonyms:(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

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Chemical Property of (+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

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Technology Process of (+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

There total 6 articles about (+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-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: 90.0%

: 915694-41-6
(+)-(1R,2R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-bicyclo[3.1.0]hexan-3-one

: 917-64-6
methyl magnesium iodide

: 915694-42-7
(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: In diethyl ether; at 0 - 20 ℃; for 4h;
DOI:10.1021/ol061959f

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

: 915694-42-7
(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 49 percent / CH₂Cl₂; hexane / 96 h / 20 °C

2: 90 percent / imidazole / CH₂Cl₂ / 0.33 h / 20 °C

3: 80 percent / DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

4: 90 percent / diethyl ether / 4 h / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; In diethyl ether; hexane; dichloromethane; 3: Swern oxidation;
DOI:10.1021/ol061959f

Reference yield:

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

: 915694-42-7
(+)-(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyldiphenylsilyloxy)-1-(tert-butyldiphenylsilyloxymethyl)-3-methyl-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / imidazole / CH₂Cl₂ / 0.33 h / 20 °C

2: 80 percent / DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

3: 90 percent / diethyl ether / 4 h / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; In diethyl ether; dichloromethane; 2: Swern oxidation;
DOI:10.1021/ol061959f