methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS No.: 111462-54-5
• Molecular Formula: C₅₂H₆₆O₁₁Si₂
• Molecular Weight: 923.26

Synonyms:methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Chemical Property of methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Chemical Property:

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Technology Process of methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

There total 2 articles about methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside 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: 81.0%

methyl 3-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside (111462-53-4) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-54-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1016/0008-6215(87)84003-X

Reference yield:

methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (78077-24-4) → methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 0.1 M sodium methoxide / methanol / 4 h / Ambient temperature

2: 81 percent / imidazol / dimethylformamide / 1 h / 0 °C

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

DOI:10.1016/0008-6215(87)84003-X

Reference yield: 89.0%

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-54-5) + 2,2-dimethoxy-propane (77-76-9) → methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-55-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(87)84003-X

upstream raw materials:

methyl 3-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside

tert-butylchlorodiphenylsilane

methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Downstream raw materials:

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

(3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

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