phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 808762-01-8
• Molecular Formula: C₃₄H₃₄O₆S
• Molecular Weight: 570.706
• Mol file: 808762-01-8.mol

Synonyms:phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

There total 2 articles about phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside 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: 99.0%

benzyl bromide (100-39-0) + phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808761-99-1) → phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808762-01-8)

Guidance literature:

phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; for 24h; Heating;

DOI:10.1021/ja0471931

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808762-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / p-TsOH / dimethylformamide / 3 h / 60 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 99 percent / tetrahydrofuran / 24 h / Heating

With sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0471931

Reference yield: 90.0%

phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808762-01-8) → phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside (850647-86-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 0 ℃; for 5h;

DOI:10.1021/ol050224s DOI:10.1021/ja061594u

upstream raw materials:

benzyl bromide

phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

methyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranoside

phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

phenyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-α-D-thiohept-6-enopyranoside