4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside
• CAS No.: 1593576-35-2
• Molecular Formula: C₄₂H₄₄O₆S
• Molecular Weight: 676.874

Synonyms:4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property of 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

There total 2 articles about 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-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: 94.0%

p-methylphenyl 2,3,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (851895-41-5) + p-methoxybenzyl chloride (824-94-2) → 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (1593576-35-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201308334

Reference yield:

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside (850416-39-6) → 4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (1593576-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid; triethylsilane / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With triethylsilane; sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201308334

Reference yield: 78.0%

4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (1593576-35-2) → 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-glucopyranose (1593576-57-8)

Guidance literature:

With N-iodo-succinimide; In water; acetone; at 0 ℃; for 0.5h;

DOI:10.1002/anie.201308334

upstream raw materials:

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside

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

p-methoxybenzyl chloride

Downstream raw materials:

2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-gluconamide

(5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-glucopyranose

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