N-acetylglucosaminylasparagine

Base Information

• Chemical Name: N-acetylglucosaminylasparagine
• CAS No.: 2776-93-4
• Molecular Formula: C12H21 N3 O8
• Molecular Weight: 335.314
• UNII: Q9ODP9B8O5
• DSSTox Substance ID: DTXSID401027514
• Nikkaji Number: J37.492J
• Wikipedia: Aspartylglucosamine
• Wikidata: Q4807723
• Metabolomics Workbench ID: 37273
• Mol file: 2776-93-4.mol

Synonyms:2-acetamido-1-(beta-L-aspartamido)-1,2-dideoxy-beta-D-glucose;2-acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine;4-N-2-acetamido-2-deoxy-beta-D-glucopyranosyl-L-asparagine;AADG;acetylglucosaminylasparagine;asparaginylglucosamine;aspartylglucosamine;aspartylglucosylamine;aspartylglycosamine;N(4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine;N(4)-(2-acetamido-2-deoxyglucopyranosyl)asparagine;N-(2-acetylamino)-2-deoxy-beta-D-glucopyranosyl-L-asparagine;N-acetylglucosaminylasparagine;N-ADGP-Asn

Chemical Property of N-acetylglucosaminylasparagine

Chemical Property:

• Vapor Pressure: 4.86E-31mmHg at 25°C
• Melting Point: 264-266 °C (decomp)(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 818.5°Cat760mmHg
• PKA: 2.43±0.10(Predicted)
• Flash Point: 448.8°C
• PSA: 191.44000
• Density: 1.53g/cm³
• LogP: -2.66960
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 335.13286464
• Heavy Atom Count: 23
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

2-Acetamido-2-deoxy-b-D-glucopyranosyl L-asparagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1NC(=O)CC(C(=O)O)N)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1NC(=O)C[C@@H](C(=O)O)N)CO)O)O
• Uses: 2-Acetamido-1-N-(β-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine can be used to diagnose and treat renal disease.

Technology Process of N-acetylglucosaminylasparagine

There total 6 articles about N-acetylglucosaminylasparagine 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: 81.0%

2-acetamido-1-N-(1-benzyloxy-N-benzyloxycarbonyl-4-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine (16405-05-3) → 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine (2776-93-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 5h;

DOI:10.1007/BF00954837

Reference yield:

2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1) → 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine (2776-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / H₂O; dimethylformamide / 16 h / 20 °C

2: 81 percent / H₂ / 10percent Pd/C / methanol; H₂O / 5 h

With hydrogen; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1007/BF00954837

Reference yield:

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) → 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine (2776-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / NH₄HCO₃ / H₂O / 168 h / 30 °C / other temperature, reaction time

2: 52 percent / H₂O; dimethylformamide / 16 h / 20 °C

3: 81 percent / H₂ / 10percent Pd/C / methanol; H₂O / 5 h

With hydrogen; ammonium bicarbonate; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1007/BF00954837

upstream raw materials:

2-acetamido-1-N-(1-benzyloxy-N-benzyloxycarbonyl-4-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine

2-acetamido-2-deoxy-β-D-glucopyranosylamine

N-Acetyl-D-glucosamine

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

Downstream raw materials:

N-Acetyl-D-glucosamine

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine

aspartic acid β-hydrazide

2-deoxy-2-amino glucose

Refernces

• 1、 Likhosherstov, L. M.,Novikova, O. S.,Derevitskaya, V. A.,Kochetkov, N. K.. "NEW SIMPLE SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE AND 2-ACETAMIDO-4-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE AND PREPARATION OF THEIR N-ACYL DERIVATIVES". . p. 1512 - 1517. Retrieved 2007/10/02.