[(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester
• CAS No.: 85781-29-9
• Molecular Formula: C₂₆H₄₇NO₆Si₂
• Molecular Weight: 525.833

Synonyms:[(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

Chemical Property of [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

There total 3 articles about [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester 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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + ((3R,4S,5S)-2-Hydroxy-4,5-bis-hydroxymethyl-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (85781-28-8) → [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (85781-29-9)

Guidance literature:

With pyridine; for 15h;

DOI:10.1021/ja00350a061

Reference yield:

methyl 2-amino-2,3-dideoxy-3-C-formyl-α-D-xylofuranoside-(3'R)-5-hemiacetal (84034-70-8) → [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (85781-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) NaBH₄ / 1.) MeOH(aq), 1.5 h, 2.) MeOH

2: 87 percent / pyridine / 15 h

With pyridine; sodium tetrahydroborate;

DOI:10.1021/ja00350a061

Reference yield:

2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine (42116-21-2) → [(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (85781-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) NaBH₄ / 1.) MeOH(aq), 1.5 h, 2.) MeOH

2: 87 percent / pyridine / 15 h

With pyridine; sodium tetrahydroborate;

DOI:10.1021/ja00350a061

upstream raw materials:

tert-butyldimethylsilyl chloride

((3R,4S,5S)-2-Hydroxy-4,5-bis-hydroxymethyl-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

methyl 2-amino-2,3-dideoxy-3-C-formyl-α-D-xylofuranoside-(3'R)-5-hemiacetal

2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine

Downstream raw materials:

{(1R,2R)-1-[(1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-propyl]-2-hydroxy-pent-4-enyl}-carbamic acid benzyl ester

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