(+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

Base Information

• Chemical Name: (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol
• CAS No.: 219776-38-2
• Molecular Formula: C₂₃H₃₀O₃Si
• Molecular Weight: 382.575

Synonyms:(+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

Chemical Property of (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

Chemical Property:

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Technology Process of (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

There total 6 articles about (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-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: 68.0%

tert-Butyl-diphenyl-[(1R,2R,4S,5R)-5-((S)-toluene-4-sulfinyl)-4-vinyl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethoxy]-silane (873438-45-0) → (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol (219776-38-2) + (-)-(2S,4R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

Guidance literature:

With sodium tetrahydroborate; diphenyl diselenide; In ethanol; at -10 - 0 ℃; for 3h;

DOI:10.1021/jo051459k

Reference yield: 61.0%

tert-Butyl-diphenyl-[(1R,2R,4S,5R)-5-(toluene-4-sulfonyl)-4-vinyl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethoxy]-silane (873438-17-6) → (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol (219776-38-2) + (-)-(2S,4R,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol

Guidance literature:

With sodium tetrahydroborate; diphenyl diselenide; In ethanol; at 0 - 20 ℃; for 28h;

DOI:10.1021/jo051459k

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (+)-(2S,4S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-vinyltetrahydrofuran-4-ol (219776-38-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 68 percent / NaBH₄; diphenyl diselenide / ethanol / 3 h / -10 - 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; diphenyl diselenide; In ethanol; dichloromethane;

DOI:10.1021/jo051459k

upstream raw materials:

tert-Butyl-diphenyl-[(1R,2R,4S,5R)-5-((S)-toluene-4-sulfinyl)-4-vinyl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethoxy]-silane

tert-Butyl-diphenyl-[(1R,2R,4S,5R)-5-(toluene-4-sulfonyl)-4-vinyl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethoxy]-silane

tert-butylchlorodiphenylsilane

(+)-(2R,3R,4R,5S,S_S)-3,4-epoxy-4-(p-tolylsulfinyl)-5-vinyl-tetrahydrofuran-2-methanol

Downstream raw materials:

(-)-(1S,5S,7S)-7-(tert-butyldiphenylsilyloxymethyl)-2,6-dioxabicyclo[3.3.0^4,8]octan-3-ol

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