allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside

Base Information

• Chemical Name: allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside
• CAS No.: 171865-45-5
• Molecular Formula: C₂₂H₃₀O₁₁
• Molecular Weight: 470.474

Synonyms:allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside

Chemical Property of allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside

Chemical Property:

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Technology Process of allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside

There total 2 articles about allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-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: 78.0%

benzaldehyde dimethyl acetal (1125-88-8) + allyl α-D-glucopyranosyl-(1->4)-β-D-glcopyranoside (113842-87-8) → allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside (171865-45-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1246/bcsj.68.2331

Reference yield:

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside (97777-13-4) → allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside (171865-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOMe / methanol

2: 78 percent / p-toluenesulfonic acid monohydrate (TSA) / dimethylformamide / Ambient temperature

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

DOI:10.1246/bcsj.68.2331

Reference yield:

benzyl bromide (100-39-0) + allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranoside (171865-45-5) → (2R,4aR,6R,7R,8S,8aR)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

DOI:10.1246/bcsj.68.2331

upstream raw materials:

benzaldehyde dimethyl acetal

allyl α-D-glucopyranosyl-(1->4)-β-D-glcopyranoside

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside

Downstream raw materials:

allyl O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(2,3-di-O-benzyl-6-O-trityl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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