O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

Base Information

• Chemical Name: O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate
• CAS No.: 132063-05-9
• Molecular Formula: C15H19N3O7
• Molecular Weight: 353.33
• DSSTox Substance ID: DTXSID601125437
• Wikipedia: PUGNAc
• Mol file: 132063-05-9.mol

Synonyms:N-acetylglucosaminono-1,5-lactone O-(phenylcarbamoyl)oxime;NAc-LAPCO;O-(2-acetamido-2-deoxyglucopyranosylidene)amino N-phenylcarbamate;PUGNAC

Chemical Property of O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

Chemical Property:

• PKA: 12.30±0.70(Predicted)
• PSA: 156.36000
• Density: 1.53±0.1 g/cm3(Predicted)
• LogP: -0.07180
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 353.12229995
• Heavy Atom Count: 25
• Complexity: 507

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1=NOC(=O)NC2=CC=CC=C2)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1=NOC(=O)NC2=CC=CC=C2)CO)O)O

Technology Process of O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

There total 9 articles about O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate 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: 73.0%

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate (872611-17-1) → O-(2-acetamido-2-deoxy-D-glucopyranosylidene)-amino N-phenylcarbamate (132489-69-1,132063-05-9,872611-16-0)

Guidance literature:

With ammonia; water; In methanol; at -10 ℃; for 12h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<114::AID-HLCA114>3.0.CO;2-9

Reference yield: 71.0%

O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-acetyl-D-galactopyranosylidene)amino N-phenylcarbamate (1145879-04-4) → O-(2-deoxy-2-N-acetyl-D-galactopyranosylidene)amino N-phenylcarbamate (1145878-98-3,132063-05-9,872611-16-0)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 2h;

DOI:10.1002/anie.200804583

Reference yield: 61.0%

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate (132063-04-8) → O-(2-acetamido-2-deoxy-D-glucopyranosylidene) amino-N-phenylcarbamate (132489-69-1,132063-05-9,872611-16-0)

Guidance literature:

With methanol; ammonia; for 4h;

DOI:10.1002/hlca.19900730714

upstream raw materials:

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

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

C₁₆H₂₂N₂O₁₀

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate