Phenyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside
• CAS No.: 10139-04-5
• Molecular Formula: C14H19 N O6
• Molecular Weight: 297.308
• Hs Code.: 29389090
• European Community (EC) Number: 233-393-4
• DSSTox Substance ID: DTXSID40906118
• Nikkaji Number: J208.835E
• Wikidata: Q27131215
• Metabolomics Workbench ID: 61740
• Mol file: 10139-04-5.mol

Synonyms:10139-04-5;Phenyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside;Phenyl N-Acetyl-alpha-D-glucosaminide;phenyl alpha-N-acetyl-D-glucosaminide;CHEBI:61628;phenyl 2-acetamido-2-deoxy-alpha-D-glucoside;EINECS 233-393-4;N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-phenoxytetrahydro-2H-pyran-3-yl)acetamide;C14H19NO6;beta-Phenyl-N-acetyl-alpha-D-glucosaminide;Epitope ID:141118;Phenyl 2-acetamido-2-deoxy-a-D-glucopyranoside;SCHEMBL432365;DTXSID40906118;P0130;D91904;phenyl-2-acetamido-2-deoxy-alpha-d-glucopyranoside;Q27131215;alpha-D-Glucopyranoside, phenyl 2-(acetylamino)-2-deoxy-;Phenyl 2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

Chemical Property of Phenyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 2.77E-15mmHg at 25°C
• Melting Point: 241 °C
• Boiling Point: 600.8oC at 760 mmHg
• PKA: 12.85±0.70(Predicted)
• Flash Point: 317.2oC
• PSA: 108.25000
• Density: 1.38g/cm3
• LogP: -0.60000
• Storage Temp.: 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 297.12123733
• Heavy Atom Count: 21
• Complexity: 346

Purity/Quality:

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

Phenyl 2-acetamido-2-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=CC=C2)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OC2=CC=CC=C2)CO)O)O

Technology Process of Phenyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

There total 9 articles about Phenyl 2-acetamido-2-deoxy-alpha-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: 99.0%

phenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-mannopyranoside (4148-73-6,13089-19-5,13089-21-9,13089-43-5,13089-70-8,23646-65-3,30657-66-0) → Phenyl 2-acetamido-2-desoxy-α-D-mannopyranosid (4291-19-4,4366-43-2,5574-80-1,10139-04-5,13089-18-4,23646-66-4)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.333333h;

DOI:10.3762/bjoc.8.48

Reference yield: 90.0%

1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose (13089-19-5) → phenyl-2-acetamido-2-deoxy-α-D-glucopyranoside (10139-04-5)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1007/s10600-020-02986-4

Reference yield:

→ phenyl-2-acetamido-2-deoxy-α-D-glucopyranoside (10139-04-5)

Guidance literature:

With sodium hydroxide; acetone;

upstream raw materials:

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

1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose

phenol

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-mannopyrano)-[2,1:4',5']-2-oxazoline

Refernces

• 1、 Krenek, Karel,Simon, Petr,Weignerova, Lenka,Fliedrova, Barbora,Kuzma, Marek,Kren, Vladimir. "Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D- mannopyranosides from ManNAc-oxazoline". . p. 428 - 432. Retrieved 2012/05/05.