methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 1423498-07-0
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419
• Mol file: 1423498-07-0.mol

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 5 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-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: 68.0%

methanol (67-56-1) + p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-D-glucopyranoside → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1423498-07-0) + Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-D-glucopyranoside; With silver trifluoromethanesulfonate; p-toluenesulfonyl chloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

methanol; In dichloromethane; at -78 ℃; Overall yield = 76 %; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201203418

Reference yield:

methanol (67-56-1) + p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-β-D-glucopyranoside (1423496-86-9) → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1423498-07-0) + Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-β-D-glucopyranoside; 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 = 88percent; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201906297

Reference yield:

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1423498-07-0) + Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / acetonitrile / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: N-iodo-succinimide / dichloromethane / 0.5 h / -40 °C / Molecular sieve; Inert atmosphere

3.2: -40 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; camphor-10-sulfonic acid; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/anie.202013909

upstream raw materials:

methanol

p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-β-D-glucopyranoside

benzaldehyde dimethyl acetal

p-methylphenyl 4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside