N-Acetyl-4,7-dideoxyneuraminic acid

Base Information

• Chemical Name: N-Acetyl-4,7-dideoxyneuraminic acid
• CAS No.: 117193-44-9
• Molecular Formula: C₁₁H₁₉NO₇
• Molecular Weight: 277.274
• DSSTox Substance ID: DTXSID10922320
• Mol file: 117193-44-9.mol

Synonyms:N-acetyl-4,7-dideoxyneuraminic acid;N-ADDNA

Chemical Property of N-Acetyl-4,7-dideoxyneuraminic acid

Chemical Property:

• Vapor Pressure: 3.45E-20mmHg at 25°C
• Boiling Point: 659.4°Cat760mmHg
• Flash Point: 352.6°C
• PSA: 139.81000
• Density: 1.44g/cm³
• LogP: -0.97310
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 277.11615195
• Heavy Atom Count: 19
• Complexity: 348

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CCC(OC1CC(CO)O)(C(=O)O)O
• Isomeric SMILES: CC(=O)N[C@H]1CC[C@](O[C@@H]1CC(CO)O)(C(=O)O)O

Technology Process of N-Acetyl-4,7-dideoxyneuraminic acid

There total 3 articles about N-Acetyl-4,7-dideoxyneuraminic 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:

Methyl-5-(acetylamino)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester (88481-35-0) → 5-Acetamido-3,4,5,7-tetradesoxy-β-D-lyxo-2-nonulopyranosidonsaeure (117193-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) DBU / 1) DMF, 2.5 h, 40 deg C, 2) 0.5 h, r.t.

2: (n-C₄H₉)3SnH / xylene / 2.5 h / 120 °C

3: 1) 1-n NaOH, 2) 0.025-m HCl, dowex 50H(+) / 1) C₂H₅OH, 2 h, 40 deg C, 2) C₂H₅OH, 2 h, 80 deg C

With hydrogenchloride; sodium hydroxide; dowex 50H(+); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In xylene;

DOI:10.1007/BF00810094

Reference yield:

Methyl-5-acetamido-3,5-didesoxy-4,7-di-O-(methyldithiocarboxy)-8,9-(methylethyliden)-β-D-glycero-D-galakto-2-nonulopyranosidonsaeuremethylester (117193-42-7) → 5-Acetamido-3,4,5,7-tetradesoxy-β-D-lyxo-2-nonulopyranosidonsaeure (117193-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (n-C₄H₉)3SnH / xylene / 2.5 h / 120 °C

2: 1) 1-n NaOH, 2) 0.025-m HCl, dowex 50H(+) / 1) C₂H₅OH, 2 h, 40 deg C, 2) C₂H₅OH, 2 h, 80 deg C

With hydrogenchloride; sodium hydroxide; dowex 50H(+); tri-n-butyl-tin hydride; In xylene;

DOI:10.1007/BF00810094

Reference yield:

Methyl-5-acetamido-3,4,5,7-tetradesoxy-8,9-O-(methylethyliden)-β-D-lyxo-2-nonulopyranosidonsaeuremethylester → 5-Acetamido-3,4,5,7-tetradesoxy-β-D-lyxo-2-nonulopyranosidonsaeure (117193-44-9)

Guidance literature:

With hydrogenchloride; sodium hydroxide; dowex 50H(+); Yield given. Multistep reaction; 1) C₂H₅OH, 2 h, 40 deg C, 2) C₂H₅OH, 2 h, 80 deg C;

DOI:10.1007/BF00810094

upstream raw materials:

Methyl-5-(acetylamino)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester

Methyl-5-acetamido-3,5-didesoxy-4,7-di-O-(methyldithiocarboxy)-8,9-(methylethyliden)-β-D-glycero-D-galakto-2-nonulopyranosidonsaeuremethylester

Refernces