1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose
• CAS No.: 93417-42-6
• Molecular Formula: C₃₁H₃₈O₁₇
• Molecular Weight: 682.633

Synonyms:1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property of 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose

There total 4 articles about 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose 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: 90.0%

benzaldehyde dimethyl acetal (1125-88-8) + 1,2,3,6-tetra-O-acetyl-4-O-(2',3'-di-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (72718-62-8,81661-67-8,102281-77-6,120852-02-0,93417-43-7) → 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose (93417-42-6)

Guidance literature:

With p-toluenesulfonic acid monohydride; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(84)85189-7

Reference yield: 86.0%

acetic anhydride (108-24-7) + (4',6'-O-benzylidene)-4-O-α-D-glucopyranosyl-D-glucopyranoside → 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose (93417-42-6)

Guidance literature:

With sodium acetate; for 0.333333h; Heating;

DOI:10.1016/0008-6215(84)85189-7

Reference yield:

Maltose + benzaldehyde dimethyl acetal (1125-88-8) → 1,2,2',3,3',6-hexa-O-acetyl-4',6'-O-benzylidene-α-maltose + 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose (93417-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 6 h / 40 °C / 30 Torr

2: sodium acetate / Reflux

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

DOI:10.1021/jm101525j

upstream raw materials:

benzaldehyde dimethyl acetal

1,2,3,6-tetra-O-acetyl-4-O-(2',3'-di-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranosyl)-β-D-glucopyranose

1,2,2',3,3',4',6-hepta-O-acetyl-6'-O-triphenylmethyl-β-maltose

O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose

1,2,3,6-tetra-O-acetyl-4-O-(2,3,4-tri-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranosyl)-β-D-glucopyranose

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