(3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one

Base Information

• Chemical Name: (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one
• CAS No.: 454474-60-3
• Molecular Formula: C₄₃H₄₆O₆Si
• Molecular Weight: 686.92

Synonyms:(3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one

Chemical Property of (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one

There total 3 articles about (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one 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:

6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-α-D-galactopyranose (454474-59-0) → (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one (454474-60-3)

Guidance literature:

6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-α-D-galactopyranose; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -70 ℃; for 0.5h;

With triethylamine; In dichloromethane; dimethyl sulfoxide; at -70 - 0 ℃; Further stages.;

DOI:10.1021/jo020211h

Reference yield:

2,3,4-tri-O-benzyl-D-galactopyranose (48229-09-0) → (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one (454474-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / imidazole / dimethylformamide / 28 h / 20 °C

2.1: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / -70 °C

2.2: triethylamine / dimethylsulfoxide; CH₂Cl₂ / -70 - 0 °C

With 1H-imidazole; oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(1-tert-butyldiphenylsilyloxymethyl)-tetrahydropyran-2-one (454474-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / imidazole / dimethylformamide / 28 h / 20 °C

2.1: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / -70 °C

2.2: triethylamine / dimethylsulfoxide; CH₂Cl₂ / -70 - 0 °C

With 1H-imidazole; oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

upstream raw materials:

6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-α-D-galactopyranose

2,3,4-tri-O-benzyl-D-galactopyranose

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,3R,4R,5R,6S,9S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane

(2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

(S)-4-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-4-methoxymethoxy-butan-1-ol

(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-2-(1-tert-butyldiphenylsilyloxymethyl)-6-decyltetrahydropyran

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