N-acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Base Information

• Chemical Name: N-acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate
• CAS No.: 73208-82-9
• Molecular Formula: C₂₂H₃₁NO₁₄
• Molecular Weight: 533.486
• Hs Code.: 2940000080
• Mol file: 73208-82-9.mol

Synonyms:5-(AcetylaMino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate; (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate; Methyl 5-Acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonate N-Acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate; methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate; 2,4,7,8,9-Penta-O-acetyl-a-D-neuraminic acid methyl ester;

Chemical Property of N-acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 157°C(lit.)
• Boiling Point: 582.771oC at 760 mmHg
• Flash Point: 306.249oC
• PSA: 196.13000
• Density: 1.313g/cm3
• LogP: -0.53850
• Storage Temp.: ?20°C
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

98%, ^*data from raw suppliers

N-Acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected Neuraminic Acid derivative.

Technology Process of N-acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

There total 1 articles about N-acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate 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-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate (6931-68-6,73208-82-9,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,72690-21-2)

Guidance literature:

In acetonitrile; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/0008-6215(89)84135-7

Reference yield: 96.0%

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) + 4-tercbutyl-cyclohexanone (98-53-3) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(4-tert-butyl-1-hydroxy-cyclohexyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/anie.200601209

Reference yield: 95.0%

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2)

Guidance literature:

In dichloromethane; at 420 ℃; under 48.7549 - 67.5068 Torr; Pyrolysis;

DOI:10.1021/jo900224t

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

Downstream raw materials:

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

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

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

Refernces