2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside
• CAS No.: 142072-12-6
• Molecular Formula: C10H18N4O6
• Molecular Weight: 290.276
• Hs Code.: 2938909090
• Nikkaji Number: J1.512.246C
• Wikidata: Q27467868
• Mol file: 142072-12-6.mol

Synonyms:142072-12-6;2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside;beta-D-Glucopyranoside, 2-azidoethyl 2-(acetylamino)-2-deoxy-;N-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;2-Azidoethyl 2-(Acetylamino)-2-Deoxy-Beta-D-Glucopyranoside;SCHEMBL17287178;AKOS037646739;AC-32443;AS-70565;CS-0214526;T70268;Q27467868

Chemical Property of 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• PSA: 161.49000
• LogP: -1.44994
• Storage Temp.: <0°C
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 290.12263431
• Heavy Atom Count: 20
• Complexity: 375

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Azidoethyl 2-acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCCN=[N+]=[N-])CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OCCN=[N+]=[N-])CO)O)O
• Uses: 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside could be a useful reactant for multipotent protein activation.

Technology Process of 2-Azidoethyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

There total 6 articles about 2-Azidoethyl 2-Acetamido-2-deoxy-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: 95.0%

2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (142072-11-5) → 2'-azidoethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (142072-12-6)

Guidance literature:

2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside; With sodium methylate; In methanol; at 20 ℃; for 4h;

In methanol;

DOI:10.1021/ac102781u

Reference yield:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → 2'-azidoethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (142072-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

1.2: 19 h / 20 °C

2.1: sodium methylate / methanol / 4 h / 20 °C

2.2: Amberlyst 15

With sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ac102781u

Reference yield:

2-bromoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (85193-58-4) → 2'-azidoethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (142072-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃; tetrabutylammonium iodide / dimethylsulfoxide

2: NaOMe / methanol / 1 h / 20 °C

With sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; In methanol; dimethyl sulfoxide;

DOI:10.1021/ol070250l

upstream raw materials:

2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

2-bromoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

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

Downstream raw materials:

2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

C₂₄H₃₆N₂O₁₃

2-(benzyloxycarbonyl)aminoethyl 2-acetylamino-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Adamiak, Kathrin,Anders, Thorsten,Henze, Manja,Keul, Helmut,Moeller, Martin,Elling, Lothar. "Chemo-enzymatic synthesis of functionalized oligomers of N-acetyllactosamine glycan derivatives and their immobilization on biomaterial surfaces". . p. 108 - 114. Retrieved 2012.
• 2、 Norberg, Oscar,Deng, Lingquan,Aastrup, Teodor,Yan, Mingdi,Ramstroem, Olof. "Photo-click immobilization on quartz crystal microbalance sensors for selective carbohydrate-protein interaction analyses". experimental part. p. 1000 - 1007. Retrieved 2011/10/09.