(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

Base Information

Chemical Name:(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one
CAS No.:139391-31-4
Molecular Formula:C₁₉H₂₈O₄Si
Molecular Weight:348.514
Hs Code.:

Synonyms:(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

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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,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

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Technology Process of (1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

There total 17 articles about (1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-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: 96.0%

: 139342-54-4
(-)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139391-31-4
(1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(01)91030-0

Reference yield: 96.0%

: 115140-20-0,129829-54-5,139342-54-4
(+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139391-31-4,139491-27-3
(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M

Reference yield:

: 88708-22-9,94482-73-2,94482-75-4,95530-78-2
(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one

: 139391-31-4,139491-27-3
(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: TMSOTf

2: mCPBA / CHCl₃

3: HSO₃F / CH₂Cl₂

4: 96 percent / 1H-imidazole / dimethylformamide

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; fluorosulphonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M