methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside
• CAS No.: 1272439-31-2
• Molecular Formula: C₃₄H₄₀O₁₁
• Molecular Weight: 624.685
• Mol file: 1272439-31-2.mol

Synonyms:methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside

There total 2 articles about methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-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: 51.0%

methyl 4-O-(2,3,4,6-tetra-O-trimethysilyl-α-D-glucopyranosyl)-2,3,6-O-trimethysilyl-α-D-glucopyranoside (1272439-25-4) + benzaldehyde (100-52-7) → methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside (1272439-31-2)

Guidance literature:

With triethylsilane; iron (III) chloride hexahydrate; In dichloromethane; acetonitrile; at 0 - 20 ℃; regioselective reaction;

DOI:10.1039/c0cc04398b

Reference yield:

methyl α-D-glucopyranosyl-(1->4)-α-D-glucopyranoside (744-05-8,4198-49-6,7216-69-5,7216-73-1,21973-65-9,35438-39-2,58462-71-8,66101-74-4,66101-75-5,67145-39-5,67145-40-8,70399-66-5,70427-91-7,70428-28-3,80446-84-0,81131-44-4,84129-57-7,92282-08-1,93221-82-0,114580-08-4,114817-99-1,117064-58-1,117064-59-2,118493-11-1,118493-12-2,118493-13-3,127253-90-1,127641-09-2,130192-72-2,136890-91-0,145680-83-7,146683-50-3) → methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside (1272439-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 20 °C

2: triethylsilane; iron (III) chloride hexahydrate / dichloromethane; acetonitrile / 0 - 20 °C

With pyridine; triethylsilane; iron (III) chloride hexahydrate; In dichloromethane; acetonitrile;

DOI:10.1039/c0cc04398b

Reference yield: 100.0%

methyl 4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-benzyl-α-D-glucopyranoside (1272439-31-2) + acetic anhydride (108-24-7) → methyl 4-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside (1272439-38-9)

Guidance literature:

With pyridine;

DOI:10.1039/c0cc04398b

upstream raw materials:

methyl 4-O-(2,3,4,6-tetra-O-trimethysilyl-α-D-glucopyranosyl)-2,3,6-O-trimethysilyl-α-D-glucopyranoside

benzaldehyde

methyl α-D-glucopyranosyl-(1->4)-α-D-glucopyranoside

Downstream raw materials:

methyl 4-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside