(2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• CAS No.: 1113-83-3
• Molecular Formula: C₁₁H₁₉NO₁₀
• Molecular Weight: 325.273
• Hs Code.: 29329990
• Nikkaji Number: J1.072.451A
• Wikipedia: N-Glycolylneuraminic_acid
• Wikidata: Q309533
• Metabolomics Workbench ID: 37455
• ChEMBL ID: CHEMBL496421
• Mol file: 1113-83-3.mol

Synonyms:GcNeu;N-glycoloylneuraminic acid;N-glycolylneuraminic acid;N-glycolylneuraminic acid, (alpha-D-Gal)-isomer;NGNA

Chemical Property of (2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 3.24E-34mmHg at 25°C
• Melting Point: 188-190°C
• Refractive Index: 1.62
• Boiling Point: 884.2oC at 760 mmHg
• PKA: 2.41±0.54(Predicted)
• Flash Point: 488.6oC
• PSA: 197.01000
• Density: 1.75 g/cm3
• LogP: -4.50850
• Storage Temp.: −20°C
• Solubility.: Water (Sparingly)
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 325.10089580
• Heavy Atom Count: 22
• Complexity: 418

Purity/Quality:

99%, ^*data from raw suppliers

N-Glycolylneuraminic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O
• Uses: Regulation of N-glycolylneuraminic acid biosynthesis in rat and mouse liver. Glycolylneuraminic acid, a component of non-human milk and colostrums, is used as a reference to analyse changes of the glycome during lactation. Glycolylneuraminic acid, a xenoantigen, is involved in antigenic reactions (antibody-mediated hyperacute rejection) during xenotransplantion.

Technology Process of (2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid

There total 1 articles about (2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid 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:

→ N-glycolyl-neuraminic acid (1113-83-3)

Guidance literature:

1. Neuraminsaeuremethylglycosid (aus Rindersubmaxillarismucin) u. 1,3-Dioxolan-2,4-dion (aus Glykolsaeure u. Phosgen), 2. wss. HCl;

DOI:10.1515/bchm2.1969.350.1.111

Reference yield:

N-glycolyl-neuraminic acid (1113-83-3) → (4S,5R,6R,7S,8R)-2-[(Z)-Benzyloxyimino]-4,6,7,8,9-pentahydroxy-5-(2-hydroxy-acetylamino)-nonanoic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: Dowex 50 x 8 (H⁽¹⁺⁾ form) / 2 h / Ambient temperature

2: 1-dimethylamino-2-propanol / methanol; pyridine / 0.17 h / 50 °C

With 1-methyl-2-N,N-dimethylaminoethanol; Dowex 50 x 8 (H⁽¹⁺⁾ form); In pyridine; methanol;

DOI:10.1016/S0008-6215(00)82581-1

Reference yield:

methanol (67-56-1) + N-glycolyl-neuraminic acid (1113-83-3) → N-glycolyl-neuraminic acid methyl ester (117300-29-5)

Guidance literature:

With Dowex 50 x 8 (H⁽¹⁺⁾ form); for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(00)82581-1

Downstream raw materials:

N-glycolyl-neuraminic acid methyl ester

Refernces