Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside
• CAS No.: 166516-67-2
• Molecular Formula: C12H15N3O4S
• Molecular Weight: 297.335
• Mol file: 166516-67-2.mol

Synonyms:phenyl 2-aminobenzyl ether;2-phenoxymethyl-aniline;Phenyl-(2-amino-benzyl)-aether;(o-Aminobenzyl)-phenyl-ether;2-(phenoxymethyl)phenylamine;Benzenamine,2-(phenoxymethyl);2-Phenoxymethyl-anilin;

Chemical Property of Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside

Chemical Property:

• PSA: 144.97000
• LogP: 0.34936

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside

There total 17 articles about Phenyl2-azido-2-deoxy-1-thio-beta-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: 97.0%

phenyl 4,6-di-O-acetyl-2-azido-3-O-benzoyl-2-deoxy-1-thio-β-D-glucopyranoside (405290-57-5) → phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (166516-67-2)

Guidance literature:

With sodium methylate; In methanol; at 23 ℃; for 12h;

DOI:10.1081/CAR-100108280

Reference yield: 89.0%

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside → phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (166516-67-2)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside; With potassium carbonate; In methanol; water; at 20 - 60 ℃; for 17h;

With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate; copper(II) sulfate; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/acs.joc.6b00177

Reference yield: 47.0%

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside (371123-22-7) → phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (166516-67-2)

Guidance literature:

With dmap; triflic azide; In methanol; dichloromethane; at 20 ℃; for 16h;

upstream raw materials:

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

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

phenyl 4,6-di-O-acetyl-2-azido-3-O-benzoyl-2-deoxy-1-thio-β-D-glucopyranoside

phenyl 2,3:4,6-bis-O-isopropylidene-1-thio-β-D-mannopyranoside

Downstream raw materials:

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

Refernces

• 1、 Potter, Garrett T.,Jayson, Gordon C.,Miller, Gavin J.,Gardiner, John M.. "An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate". . p. 3443 - 3446. Retrieved 2016.
• 2、 Bower, John F.,Galan, M. Carmen,Henderson, Alexander S.. "Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination". supporting information. p. 3012 - 3016. Retrieved 2020/05/08.