3-acetamido-4-hydroxy-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

Base Information

• Chemical Name: 3-acetamido-4-hydroxy-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS No.: 24967-27-9
• Molecular Formula: C₁₁H₁₇NO₈
• Molecular Weight: 291.258
• European Community (EC) Number: 246-550-7
• Mol file: 24967-27-9.mol

Synonyms:N-acetyl-2,3-dehydro-2-deoxyneuraminic acid;NADNA cpd

Chemical Property of 3-acetamido-4-hydroxy-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.27E-27mmHg at 25°C
• Melting Point: 227-228
• Boiling Point: 773.4ºC at 760 mmHg
• PKA: 3.90±0.70(Predicted)
• Flash Point: 421.6ºC
• PSA: 156.55000
• Density: 1.58g/cm3
• LogP: -2.67570
• Storage Temp.: −20°C
• Solubility.: H2O: soluble50mg/mL, clear, colorless
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 291.09541650
• Heavy Atom Count: 20
• Complexity: 409

Purity/Quality:

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

N-Acetyl-2,3-dehydro-2-deoxyneuraminic Acid, Sodium Salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)O
• Uses: Neuraminidase (sialidase) inhibitor N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is a bacterial, viral, and mammalian neuraminidase inhibitor. It can be used in biological study of knockdown of Neu4 and injection of sialidase inhibitor such as DANA resulted in impairment of long-term potentiation at mossy fiber-CA3 synapses and hippocampus-dependent spatial memory in rats.

Technology Process of 3-acetamido-4-hydroxy-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

There total 12 articles about 3-acetamido-4-hydroxy-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-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: 85.0%

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) → 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (24967-27-9,79026-37-2,108675-60-1,108675-61-2,108675-62-3) + 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid (41976-42-5)

Guidance literature:

With barium dihydroxide; water; at 90 ℃; for 18h;

DOI:10.1016/S0957-4166(99)00552-2

Reference yield: 73.0%

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) → 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (24967-27-9,79026-37-2,108675-60-1,108675-61-2,108675-62-3)

Guidance literature:

With methanol; sodium methylate; for 0.5h; Ambient temperature;

DOI:10.1016/0008-6215(82)85022-2

Reference yield:

cytidine-5'-monophosphono-N-acetylneuraminic acid (3063-71-6) → 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (24967-27-9,79026-37-2,108675-60-1,108675-61-2,108675-62-3)

Guidance literature:

In N,N-dimethyl-formamide; at 105 ℃; for 6h;

upstream raw materials:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid)

ethanol

Downstream raw materials:

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Neu5AcαOMe

2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid

(2R,3R,4S)-3-acetamido-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

Refernces

• 1、 -. "SIALIDASE INHIBITORS AND PREPARATION THEREOF". Paragraph 0142; 0148; 0150; 0151. . Retrieved 2018/11/22.
• 2、 Xu, Guogang,Kiefel, Milton J.,Wilson, Jennifer C.,Andrew, Peter W.,Oggioni, Marco R.,Taylor, Garry L.. "Three streptococcus pneumoniae sialidases: Three different products". supporting information; experimental part. p. 1718 - 1721. Retrieved 2011/04/17.