(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

Base Information

Chemical Name:(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol
CAS No.:144677-79-2
Molecular Formula:C₂₀H₃₂O₅Si
Molecular Weight:380.557
Hs Code.:

Synonyms:(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

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Chemical Property of (1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

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Technology Process of (1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

There total 5 articles about (1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-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: 95.0%

: 144677-78-1
(1S,3R,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-one

: 144677-79-2
(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃;
DOI:10.1016/S0040-4039(00)79144-1

Reference yield:

: 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

: 144677-79-2
(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / imidazole / dimethylformamide

2: 1) (Me₃Si)2NK / THF, -78 deg C

3: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

4: 95 percent / NaBH₄ / methanol / 0 °C

With 1H-imidazole; sodium tetrahydroborate; titanium tetrachloride; potassium hexamethylsilazane; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)79144-1

Reference yield:

: 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

: 144677-79-2
(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1) (Me₃Si)2NK / THF, -78 deg C

2: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

3: 95 percent / NaBH₄ / methanol / 0 °C

With sodium tetrahydroborate; titanium tetrachloride; potassium hexamethylsilazane; In methanol; dichloromethane;
DOI:10.1016/S0040-4039(00)79144-1