phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 277756-86-2
• Molecular Formula: C₂₆H₂₅N₃O₄S
• Molecular Weight: 475.568
• Mol file: 277756-86-2.mol

Synonyms:phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

There total 15 articles about phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-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: 98.0%

benzyl bromide (100-39-0) + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0) → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-86-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 0.666667h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield: 89.0%

benzyl bromide (100-39-0) + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-86-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 4.5h;

DOI:10.1021/acs.joc.7b00470

Reference yield: 80.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-mannopyranoside (848397-74-0) → phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-86-2)

Guidance literature:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-mannopyranoside; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.75h; Inert atmosphere;

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02669

upstream raw materials:

benzyl bromide

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

thiophenol

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

phenyl 2-azido-3,6-di-O-benzyl-4-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-β-D-glucopyranoside

C₄₆H₅₁N₃O₁₄

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate