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

Base Information

• Chemical Name: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 277756-84-0
• Molecular Formula: C₁₉H₁₉N₃O₄S
• Molecular Weight: 385.444
• Mol file: 277756-84-0.mol

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

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

There total 19 articles about phenyl 2-azido-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: 94.0%

phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside (1394857-30-7) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0)

Guidance literature:

With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate; In tetrahydrofuran; methanol; for 5h;

DOI:10.1021/jo300722y

Reference yield: 78.0%

phenyl N-(2,2,2-trichloroethoxy)carbonyl-2-amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0)

Guidance literature:

phenyl N-(2,2,2-trichloroethoxy)carbonyl-2-amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside; With acetic acid; zinc; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

With CF₃SO₂⁽¹⁺⁾*N₃^(1-)=CF₃SO₂N₃; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane; water; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.joc.8b02037

Reference yield: 78.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (166516-67-2) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 72h;

DOI:10.1021/jo300722y

upstream raw materials:

benzaldehyde dimethyl acetal

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

thiophenol

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

Downstream raw materials:

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

phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

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-2-deoxy-1-thio-β-D-glucopyranoside