methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• CAS No.: 16790-35-5
• Molecular Formula: C₂₈H₃₆O₁₅
• Molecular Weight: 612.585

Synonyms:methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

SDS file from LookChem

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Technology Process of methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

There total 1 articles about methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-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: 86.8%

methyl 4,6-O-benzylidene-β-D-glucopyranoside (14155-23-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (72522-53-3) + methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-2)-O-<2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1-3)>-4,6-O-benzylidene-β-D-glucopyranoside (76790-42-6) + methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (16790-35-5)

Guidance literature:

With tetramethylurea; silver trifluoromethanesulfonate; In various solvent(s); at 25 ℃; for 1.5h; Yields of byproduct given;

DOI:10.1016/S0008-6215(00)85199-X

Reference yield: 87.0%

methanesulfonyl chloride (124-63-0) + methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (16790-35-5) → methyl 2',3',4',6'-tetra-O-acetyl-4,6-O-benzylidene-3-O-(methylsulfonyl)-β-sophoroside (84730-84-7)

Guidance literature:

In pyridine; at 0 ℃;

DOI:10.1016/0008-6215(83)88267-6

Reference yield: 80.0%

methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (16790-35-5) → methyl 2',3',4',6'-tetra-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-sophoroside (84730-90-5)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 2h; Heating;

DOI:10.1016/0008-6215(83)88267-6

upstream raw materials:

methyl 4,6-O-benzylidene-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

methyl 2',3',4',6'-tetra-O-acetyl-4,6-O-benzylidene-3-O-(methylsulfonyl)-β-sophoroside

methyl 2',3',4',6'-tetra-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-sophoroside

methyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-allopyranoside

methyl 4,6-O-benzylidene-2-O-β-D-glucopyranosyl-β-D-allopyranoside

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