methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside

Base Information

• Chemical Name: methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside
• CAS No.: 155896-89-2
• Molecular Formula: C₅₅H₅₈O₁₁
• Molecular Weight: 895.059

Synonyms:methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside

Chemical Property of methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside

Chemical Property:

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Technology Process of methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside

There total 5 articles about methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside 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: 71.0%

benzyl bromide (100-39-0) + methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside (156038-69-6) → methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside (155896-89-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0008-6215(01)00299-3

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside (155896-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / p-toluenesulfonic acid / dimethylformamide / 20 - 50 °C

2: 71 percent / NaH / dimethylformamide / 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00299-3

Reference yield:

methyl β-D-cellobioside (7216-73-1) → methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside (155896-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / p-toluenesulfonic acid / dimethylformamide / 20 - 50 °C

2: 71 percent / NaH / dimethylformamide / 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00299-3

upstream raw materials:

benzyl bromide

methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

benzaldehyde dimethyl acetal

methyl β-D-cellobioside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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