methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside
• CAS No.: 175520-83-9
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 175520-83-9.mol

Synonyms:methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside

There total 5 articles about methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside 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:

methanol (67-56-1) + p-tolyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-galactopyranoside (1333393-53-5) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside (175520-83-9) + methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4)

Guidance literature:

p-tolyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-galactopyranoside; With N-iodo-succinimide; In dichloromethane; at -40 ℃; for 1h; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 0.5h; Inert atmosphere;

methanol; In dichloromethane; at -40 ℃; for 3h; Overall yield = 75percent; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201906297

Reference yield:

p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-86-3) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside (175520-83-9) + methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

1.2: 0 - 20 °C

2.1: N-iodo-succinimide / dichloromethane / 1 h / -40 °C / Inert atmosphere

2.2: 0.5 h / -40 °C / Inert atmosphere

2.3: 3 h / -40 °C / Inert atmosphere

With N-iodo-succinimide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201906297

Reference yield:

methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside (71117-36-7) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-galactopyranoside (175520-83-9)

Guidance literature:

With silver(l) oxide;

DOI:10.1021/ja01269a026

upstream raw materials:

methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside

methyl iodide

methyl beta-D-galactopyranoside

p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

Methyl 6-O-benzyl-2,3-di-O-methyl-β-D-galactopyranoside

Methyl 6-O-benzyl-2,3-di-O-methyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside