3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose
• CAS No.: 225924-55-0
• Molecular Formula: C₃₉H₄₆O₇Si
• Molecular Weight: 654.876

Synonyms:3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Chemical Property of 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Chemical Property:

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Technology Process of 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

There total 3 articles about 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 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: 79.0%

benzyl bromide (100-39-0) + 6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (225924-54-9) → 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (225924-55-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1153::AID-EJOC1153>3.0.CO;2-S

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (225924-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / imidazole / dimethylformamide / 24 h / 4 °C

2: 79 percent / NaH / dimethylformamide / Ambient temperature

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

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1153::AID-EJOC1153>3.0.CO;2-S

Reference yield:

1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (225924-46-9) → 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (225924-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / imidazole / dimethylformamide / 24 h / 4 °C

2: 79 percent / NaH / dimethylformamide / Ambient temperature

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

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1153::AID-EJOC1153>3.0.CO;2-S

upstream raw materials:

benzyl bromide

6-O-tert-butyldiphenylsilyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

tert-butylchlorodiphenylsilane

1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Downstream raw materials:

allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside

allyl 2-O-allyl-3,4-di-O-benzyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-α-D-mannopyranoside

O-(2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl) trichloroacetimidate

1,2-di-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-mannopyranose

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