(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene

Base Information

• Chemical Name: (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene
• CAS No.: 1239889-27-0
• Molecular Formula: C₂₅H₄₆O₃Si₂
• Molecular Weight: 450.809

Synonyms:(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene

Chemical Property of (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene

Chemical Property:

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Technology Process of (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene

There total 1 articles about (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene 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: 93.8%

(2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol (99838-68-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene (1239889-27-0)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2012.09.007

Reference yield: 85.9%

(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene (1239889-27-0) → (3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al (1410003-28-9)

Guidance literature:

(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tetasy.2012.09.007

Reference yield: 71.0%

(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene (1239889-27-0) → C19H32O3Si (1239889-28-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.05.069

upstream raw materials:

(2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₁₉H₃₂O₃Si

(3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al

(5S,6R)-ethyl-5-O-benzyl-6,7-di-O-tert-butyl-dimethylsilyl-5,6,7-trihydroxy-hept-2E-enoate

(5S,6R)-5-O-benzyl-6,7-O-di tert-butyl-dimethylsilyl-1,5,6,7-tetrahydroxy-hept-2E-ene

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