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

Base Information

• Chemical Name: (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol
• CAS No.: 153096-84-5
• Molecular Formula: C₃₆H₄₀O₄Si
• Molecular Weight: 564.797

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

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

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

There total 1 articles about (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-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:

(S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one (153096-71-0) + acetylenemagnesium bromide (4301-14-8) → (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol (153096-84-5) + (3S,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol

Guidance literature:

In diethyl ether; at 0 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/S0957-4166(00)80421-8

Reference yield: 70.0%

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol (153096-84-5) → (R)-2-((S)-1,2-Bis-benzyloxy-ethyl)-but-3-yne-1,2-diol (153096-82-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80421-8

Reference yield:

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-yn-3-ol (153096-84-5) → (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:

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

acetylenemagnesium bromide

Downstream raw materials:

(R)-2-((S)-1,2-Bis-benzyloxy-ethyl)-but-3-yne-1,2-diol

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

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

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