2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranoside

Base Information

• Chemical Name: 2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranoside
• CAS No.: 140428-81-5
• Molecular Formula: C16H23N3O10
• Molecular Weight: 417.373
• Hs Code.: 2934999090
• European Community (EC) Number: 812-175-8
• Nikkaji Number: J1.322.107C
• Wikidata: Q76421705
• Mol file: 140428-81-5.mol

Synonyms:140428-81-5;2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranoside;beta-D-Glucopyranoside, 2-azidoethyl, 2,3,4,6-tetraacetate;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-azidoethoxy)oxan-2-yl]methyl acetate;SCHEMBL17475614;2-Azidoethyl2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside;MFCD19981034;AKOS037643240;AS-11165;CS-0214523;T70259;2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranoside

Chemical Property of 2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranoside

Chemical Property:

• Melting Point: 113.0 to 117.0 °C
• PSA: 173.41000
• LogP: -0.15084
• Storage Temp.: 0-10°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 13
• Exact Mass: 417.13834394
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

97% ^*data from raw suppliers

2-Azidoethyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OCCN=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OCCN=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranoside

There total 21 articles about 2-Azidoethyl 2,3,4,6-Tetra-O-acetyl-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: 100.0%

2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-78-9,85193-55-1,86651-32-3,86651-40-3) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With Caswell No_. 744A; In water monomer; for 16h; Reflux;

DOI:10.1039/c9dt02614b

Reference yield: 99.0%

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-77-8) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 85 ℃; for 5h;

Reference yield: 94.0%

2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (350793-49-6) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1002/1521-3765(20010504)7:9<1868::AID-CHEM1868>3.0.CO;2-H

upstream raw materials:

2-azidoethanol

β-D-glucose pentaacetate

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

(2-azidoethyl)-2,3-di-O-acetyl-4-O-p-methoxybenzyl-β-D-glucopyranoside

(2-tert-butoxycarbonylamidoethyl) 6-O-tosyl-β-D-glucopyranoside

2-(p-nitrophenylcarbamate)-ethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-(p-nitrophenylcarbamate)-ethyl-2,3-di-O-acetyl-4-O-p-methoxybenzyl-β-D-glucopyranoside