tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 905704-43-0
• Molecular Formula: C₂₇H₂₉N₃O₄S
• Molecular Weight: 491.611
• Mol file: 905704-43-0.mol

Synonyms:tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

There total 8 articles about tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-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: 50.0%

5-azido-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol + benzyl bromide (100-39-0) → p-tolyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-thioglucopyranoside (671809-80-6) + tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (905704-43-0) + 3-azido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran-4-ol

Guidance literature:

5-azido-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol; With sodium hydride; In N,N-dimethyl-formamide; at -15 ℃; for 0.0833333h;

benzyl bromide; In N,N-dimethyl-formamide; at -15 - 20 ℃; for 0.5h;

DOI:10.1055/s-2006-939681

Reference yield:

tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside → tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (905704-43-0) + p-tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (502692-42-4)

Guidance literature:

tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside; With triethylsilane; In dichloromethane; at -15 - 20 ℃; for 0.333333h; Molecular sieve; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; at -15 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1002/asia.200900765

Reference yield:

4-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside (929040-77-7,501088-45-5) → tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (905704-43-0) + p-tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside (502692-42-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium / methanol; dichloromethane / 3 h / 20 °C

2.1: toluene-4-sulfonic acid / acetonitrile / 4 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

4.1: triethylsilane / dichloromethane / 0.33 h / -15 - 20 °C / Molecular sieve; Inert atmosphere

4.2: 2 h / -15 °C / Molecular sieve; Inert atmosphere

With triethylsilane; sodium; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/asia.200900765

upstream raw materials:

benzyl bromide

4-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Downstream raw materials:

methyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

C₆₁H₆₁N₃O₁₀S

C₆₁H₆₁N₃O₁₀S