N-Acetyl-4-deoxy-4-acetamidoneuraminic acid

Base Information

• Chemical Name: N-Acetyl-4-deoxy-4-acetamidoneuraminic acid
• CAS No.: 127099-59-6
• Molecular Formula: C₁₃H₂₂N₂O₉
• Molecular Weight: 350.326
• DSSTox Substance ID: DTXSID80155401
• Wikidata: Q83023306
• Mol file: 127099-59-6.mol

Synonyms:4-acetamido-4-deoxy-N-acetylneuraminic acid;4-ADANA;N-acetyl-4-deoxy-4-acetamidoneuraminic acid

Chemical Property of N-Acetyl-4-deoxy-4-acetamidoneuraminic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 877.7°Cat760mmHg
• Flash Point: 484.6°C
• PSA: 192.63000
• Density: 1.53g/cm³
• LogP: -2.04740
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 350.13253028
• Heavy Atom Count: 24
• Complexity: 500

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CC(OC(C1NC(=O)C)C(C(CO)O)O)(C(=O)O)O
• Isomeric SMILES: CC(=O)N[C@H]1C[C@](O[C@H]([C@@H]1NC(=O)C)[C@@H]([C@@H](CO)O)O)(C(=O)O)O

Technology Process of N-Acetyl-4-deoxy-4-acetamidoneuraminic acid

There total 3 articles about N-Acetyl-4-deoxy-4-acetamidoneuraminic 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: 60.0%

(2S,4S,5R,6R)-4,5-Bis-acetylamino-6-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (127072-89-3) → 4,5-diacetamido-3,4,5-trideoxy-D-glycero-β-D-galacto-pyranosonic acid (127099-59-6,140671-46-1)

Guidance literature:

With saponification;

DOI:10.1016/0008-6215(89)85037-2

Reference yield:

(2S,5R,6R)-5-Acetylamino-4-azido-6-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester → 4,5-diacetamido-3,4,5-trideoxy-D-glycero-β-D-galacto-pyranosonic acid (127099-59-6,140671-46-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / 10percent Pd-C / ethyl acetate

2: 60 percent / saponification

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/0008-6215(89)85037-2

Reference yield:

(2S,4R,5R,6R)-5-Acetylamino-6-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (88481-35-0,88547-03-9,110390-89-1,140195-53-5) → 4,5-diacetamido-3,4,5-trideoxy-D-glycero-β-D-galacto-pyranosonic acid (127099-59-6,140671-46-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / triphenylphosphine-diethylazodicarboxylate, 3M NH₃ / toluene; tetrahydrofuran / Ambient temperature

2: 90 percent / H₂ / 10percent Pd-C / ethyl acetate

3: 60 percent / saponification

With ammonium hydroxide; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene;

DOI:10.1016/0008-6215(89)85037-2

upstream raw materials:

(2S,4S,5R,6R)-4,5-Bis-acetylamino-6-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,4R,5R,6R)-5-Acetylamino-6-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces