(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol

Base Information

• Chemical Name: (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol
• CAS No.: 145361-69-9
• Molecular Formula: C₃₂H₄₄O₅Si
• Molecular Weight: 536.784

Synonyms:(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol

Chemical Property of (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol

Chemical Property:

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Technology Process of (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol

There total 2 articles about (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-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: 93.0%

3,4,6-tri-O-benzyl-D-arabinitol (14233-53-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol (145361-69-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.3987/COM-97-7939

Reference yield:

3,4,6-tri-O-benzyl-β-D-arabinofuranoside (60933-68-8) → (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol (145361-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaBH₄ / ethanol

2: 93 percent / Et₃N, DMAP / CH₂Cl₂

With dmap; sodium tetrahydroborate; triethylamine; In ethanol; dichloromethane;

DOI:10.3987/COM-97-7939

Reference yield: 80.0%

(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol (145361-69-9) → (3S,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-one (197861-86-2)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane;

DOI:10.3987/COM-97-7939

upstream raw materials:

3,4,6-tri-O-benzyl-D-arabinitol

tert-butyldimethylsilyl chloride

3,4,6-tri-O-benzyl-β-D-arabinofuranoside

Downstream raw materials:

(3S,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-one

(4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

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