(2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol

Base Information

• Chemical Name: (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol
• CAS No.: 153096-70-9
• Molecular Formula: C₃₆H₄₄O₄Si
• Molecular Weight: 568.828

Synonyms:(2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol

Chemical Property of (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol

Chemical Property:

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Technology Process of (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol

There total 5 articles about (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-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: 94.0%

ethylmagnesium bromide (925-90-6) + (S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one (153096-71-0) → (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol (153096-70-9)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo9716744

Reference yield:

(S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one (153096-71-0) → (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol (153096-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tetrahydrofuran / 1 h / -78 °C

2: H₂ / Pd/C / ethyl acetate / 3 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo9716744

Reference yield:

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol (153096-83-4) → (2S,3R)-1,2-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol (153096-70-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; Ambient temperature;

DOI:10.1021/jo9716744

upstream raw materials:

ethylmagnesium bromide

(S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol

Downstream raw materials:

(2R,3S)-3,4-Bis-benzyloxy-2-ethyl-butane-1,2-diol

Toluene-4-sulfonic acid (2S,3R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-pentyl ester

(2R,3S)-1-O-t-butyldiphenylsilyl-2-ethylpentane-1,2,3-triol

(2R,3S)-1-O-t-butyldiphenylsilyl-3,4-epoxy-2-ethylbutane-1,2-diol

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