4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol

Base Information

• Chemical Name: 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol
• CAS No.: 116730-42-8
• Molecular Formula: C₃₇H₄₄O₆Si
• Molecular Weight: 612.838

Synonyms:4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol

Chemical Property of 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol

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Technology Process of 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol

There total 6 articles about 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-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: 99.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol (116730-42-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88025-X

Reference yield: 94.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl 2,3-di-O-benzyl-β-D-glucopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,51842-19-4,52526-60-0,61117-12-2,87392-25-4,117605-35-3) → 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol (116730-42-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(88)85335-8

Reference yield: 92.0%

3,4-bis(benzyloxy)-5-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxymethyl)-2-methoxytetrahydropyran → 4,5-bis(benzyloxy)-2-(tert-butyldimethylsilanyloxy)-6-methoxytetrahydropyran-3-ol (116730-42-8)

Guidance literature:

With phosphomolybdic acid hydrate; silica gel; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/jo0502697

upstream raw materials:

tert-butylchlorodiphenylsilane

methyl 2,3-di-O-benzyl-β-D-glucopyranoside

methyl 2,3-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

C₄₃H₄₈O₆SSi

methyl 4-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-α-D-glucopyranoside

methyl 4-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside

methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside

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