Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
• CAS No.: 5574-80-1
• Molecular Formula: C14H19 N O6
• Molecular Weight: 297.308
• Hs Code.: 29389090
• European Community (EC) Number: 226-946-6
• DSSTox Substance ID: DTXSID40204287
• Nikkaji Number: J225.027F
• Wikidata: Q27131217
• Metabolomics Workbench ID: 61741
• Mol file: 5574-80-1.mol

Synonyms:5574-80-1;Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside;PHENYL-N-ACETYL-BETA-D-GLUCOSAMINIDE;Phenyl 2-acetamido-2-deoxy-b-D-glucopyranoside;PHENYL N-ACETYL-BETA-D-GLUCOSAMINIDE;phenyl beta-N-acetyl-D-glucosaminide;phenyl 2-acetamido-2-deoxy-beta-D-glucoside;CHEBI:61632;EINECS 226-946-6;N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenoxyoxan-3-yl]acetamide;C14H19NO6;D-Glucosaminide A;N-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-phenoxytetrahydro-2H-pyran-3-yl)acetamide;Epitope ID:141117;SCHEMBL11786108;DTXSID40204287;AKOS002688201;Phenyl N-acetyl-beta-D-glucosaminide, >=98%;Phenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside?;W-203109;Phenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside;Q27131217

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

Chemical Property:

• Vapor Pressure: 2.77E-15mmHg at 25°C
• Boiling Point: 600.8°Cat760mmHg
• Flash Point: 317.2°C
• PSA: 108.25000
• Density: 1.38g/cm³
• LogP: -0.60000
• Storage Temp.: ?20°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%min ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

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
• Uses: Phenyl 2-Acetamido-2-deoxy-b-D-glucopyranoside is a O-GlcNAcase substrate.

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

There total 19 articles about Phenyl 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: 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: 95.0%

1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose (13089-21-9) → phenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (5574-80-1)

Guidance literature:

With methanol; sodium methylate; for 1h;

DOI:10.1002/chem.200901830

Reference yield: 21.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + sodium phenoxide (139-02-6) → phenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (5574-80-1)

Guidance literature:

N-Acetyl-D-glucosamine; sodium phenoxide; With triethylamine; In water; at 20 ℃; for 0.166667h; Sealed tube;

With 2-chloro-1,3-dimethylimidazolinium chloride; In water; at -10 - 80 ℃; for 3h; Microwave irradiation; Sealed tube;

DOI:10.1039/d0ob01727b

upstream raw materials:

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

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

phenol

(2S,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate

Downstream raw materials:

phenyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside

phenyl 2-acetamido-3,4-di-O-benzoyl-6-O-tertbutyldimethylsilyl-2-deoxy-β-D-glucopyranoside

diallyl [phenyl 2-acetamido-3-O-benzoyl-2,4-dideoxy-β-L-threo-hex-4-enopyranoside-6-yl]-phosphonate

Refernces

• 1、 Tegl, Gregor,Hanson, John,Chen, Hong-Ming,Kwan, David H,Santana, Andrés G.,Withers, Stephen G.. "Facile Formation of β-thioGlcNAc Linkages to Thiol-Containing Sugars, Peptides, and Proteins using a Mutant GH20 Hexosaminidase". supporting information. p. 1632 - 1637. Retrieved 2019/01/14.
• 2、 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.