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

Base Information

• Chemical Name: (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol
• CAS No.: 153096-83-4
• Molecular Formula: C₃₆H₄₂O₄Si
• Molecular Weight: 566.813

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

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

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

There total 2 articles about (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-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: 90.0%

vinyl magnesium bromide (1826-67-1) + (S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one (153096-71-0) → (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol (153096-83-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo9716744

Reference yield:

vinyl magnesium bromide (1826-67-1) + (S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one (153096-71-0) → (3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol (153096-83-4) + (3S,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol

Guidance literature:

In diethyl ether; at 0 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

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

Reference yield: 63.0%

(3R,4S)-4,5-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol (153096-83-4) → (R)-2-((S)-1,2-Bis-benzyloxy-ethyl)-but-3-ene-1,2-diol (153096-81-2)

Guidance literature:

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

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

upstream raw materials:

vinyl magnesium bromide

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

Downstream raw materials:

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

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

(4R)-4-[(1S)-1,2-bis(benzyloxy)ethyl]-4-hydroxytetrahydrofuran-2-one

(3R,4S)-4,5-bis(benzyloxy)-3(tert-butyldiphenylsilyloxymethyl)-3-hydroxypentanenitrile

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