(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

Base Information

Chemical Name:(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol
CAS No.:577749-42-9
Molecular Formula:C₂₈H₃₅BrO₄SSi
Molecular Weight:575.639
Hs Code.:

Synonyms:(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

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Chemical Property of (2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

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Technology Process of (2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

There total 1 articles about (2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-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: 78.0%

: 577749-34-9
(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-1,5-bis-(tert-butyl-diphenyl-silanyloxy)-hexan-3-ol

: 577749-42-9
(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 20 ℃;
DOI:10.1021/jo026892y

Reference yield: 90.0%

: 77-76-9
2,2-dimethoxy-propane

: 577749-42-9
(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

: 577749-43-0
[(S)-1-Benzenesulfinylmethyl-2-((4R,5S)-5-bromo-2,2-dimethyl-[1,3]dioxan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: With camphor-10-sulfonic acid; In acetone; at 20 ℃;
DOI:10.1021/jo026892y

Reference yield:

: 577749-42-9
(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

: (S)-3-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-2-(tert-butyl-diphenyl-silanyloxy)-propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / camphor-10-sulfonic acid / acetone / 20 °C

2: 75 percent / NaN₃ / dimethylsulfoxide / 80 °C

3: (CF₃CO)2O; Et₃N / CH₂Cl₂ / 20 °C

With sodium azide; camphor-10-sulfonic acid; triethylamine; trifluoroacetic anhydride; In dichloromethane; dimethyl sulfoxide; acetone; 3: Pummerer rearrangement;
DOI:10.1021/jo026892y