(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol
CAS No.:476315-81-8
Molecular Formula:C₂₂H₃₀O₃Si
Molecular Weight:370.564
Hs Code.:

Synonyms:(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

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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 (2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

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Technology Process of (2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

There total 10 articles about (2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-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: 91.0%

: 476315-80-7
(2S,3S,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-iodo-2-methyl-tetrahydro-furan-3-ol

: 476315-81-8
(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

Guidance literature:: With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; for 5h;
DOI:10.1016/S0040-4039(02)01518-6

Reference yield: 59.0%

: 937723-61-0
C₂₂H₂₈O₂Si

: 476315-81-8
(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

Guidance literature:: C₂₂H₂₈O₂Si; In tetrahydrofuran; at 0 ℃; for 16h;

With sodium hydroxide; dihydrogen peroxide; at 20 ℃; for 6h; Further stages.;
DOI:10.1016/j.tetlet.2007.03.014

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 476315-81-8
(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

3.1: 77 percent / mesyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -20 - 40 °C

4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 - 0 °C

4.2: 85 percent / TMEDA / tetrahydrofuran / 12 h / 20 °C

5.1: ThxBH₂ / tetrahydrofuran / 16 h / 0 °C

5.2: 59 percent / aq. NaOH; aq. H₂O₂ / 6 h / 20 °C

With dmap; tert.-butyl lithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2007.03.014