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

Base Information

Chemical Name:(+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol
CAS No.:915694-39-2
Molecular Formula:C₂₇H₃₈O₄Si
Molecular Weight:454.682
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol

There total 2 articles about (+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol 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: 60.0%

: 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

: 75-24-1
trimethylaluminum

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

Guidance literature:: In dichloromethane; at 20 ℃; for 96h;
DOI:10.1080/15257770701508612

Reference yield:

: 303963-92-0
(3aR,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 84 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

2.1: Et₂Zn / CH₂Cl₂; hexane / 0.5 h / 0 °C

2.2: 81 percent / CH₂Cl₂; hexane / 6.5 h / 0 - 20 °C

3.1: 49 percent / CH₂Cl₂; hexane / 96 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; diethylzinc; In methanol; hexane; dichloromethane; 2.2: Simmons-Smith cyclopropanation;
DOI:10.1021/ol061959f