(2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: (2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate
• CAS No.: 22900-11-4
• Molecular Formula: C₁₂H₂₁NO₉
• Molecular Weight: 323.3
• European Community (EC) Number: 700-205-1,607-180-5
• DSSTox Substance ID: DTXSID80428304
• Nikkaji Number: J1.111.556J
• Wikidata: Q82241126
• Mol file: 22900-11-4.mol

Synonyms:22900-11-4;N-Acetylneuraminic acid methyl ester;(2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate;50998-13-5;CID 7173831;N-Acetyl-D-neuraminic acid methyl ester;MFCD08276447;EC 700-205-1;SCHEMBL126536;Methyl N-acetyl-beta-neuraminate;DTXSID80428304;BKZQMWNJESHHSA-AGNBLMTLSA-N;Methyl (2S,4S,5R,6R)-5-(acetylamino)-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate hydrate;Methyl (2S,4S,5R,6R)-5-(acetylamino)-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylate hydrate;AS-11185;beta-Neuraminic acid, N-acetyl-, methyl ester;T70600;J-014891;Methyl 5-Acetamido-3,5-dideoxy-beta-D-glycero-D-galacto-2-nonulopyranosylonate

Chemical Property of (2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.86E-22mmHg at 25°C
• Melting Point: 193.5-194.5°C
• Refractive Index: -27.5 ° (C=1, H2O)
• Boiling Point: 693.8°C at 760 mmHg
• PKA: 10.40±0.70(Predicted)
• Flash Point: 373.4°C
• PSA: 165.78000
• Density: 1.51g/cm³
• LogP: -3.39250
• Storage Temp.: Freezer
• Water Solubility.: Slightly soluble in water
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 323.12163125
• Heavy Atom Count: 22
• Complexity: 417

Purity/Quality:

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

N-Acetylneuraminic Acid Methyl Ester >95.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)OC)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)OC)O)O
• Uses: Derivative of Neuraminic Acid

Technology Process of (2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate

There total 55 articles about (2S,4S,5R,6R)-methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate 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: 100.0%

methanol (67-56-1) + sialic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → (2R,3R,4S)-3-acetamido-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid (22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2,20298-35-5)

Guidance literature:

With IR(H⁺)resin; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.077

Reference yield: 100.0%

methanol (67-56-1) + N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2)

Guidance literature:

With IR₁₂₀(H+); for 15h;

DOI:10.1055/s-2008-1072649

Reference yield: 100.0%

N-acetyl neuraminic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → methyl (4S,5R,6S)-5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2)

Guidance literature:

With AG 50W-x8; In methanol; at 45 ℃;

upstream raw materials:

diazomethane

N-acetylneuraminic acid

methanol

N-acetyl neuraminic acid

Downstream raw materials:

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester

N-acetylneuraminic acid methyl ester

methyl [2-O-(2-formyl-4-nitrophenyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-galacto-2-nonulopyranosid]onate

methyl (methyl 5-amino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Refernces

• 1、 Hribernik, Nives,Tamburrini, Alice,Falletta, Ermelinda,Bernardi, Anna. "One pot synthesis of thio -glycosides via aziridine opening reactions". supporting information. p. 233 - 247. Retrieved 2021/01/14.
• 2、 Kabotso, Daniel E. K.,Kabotso, Daniel E. K.,Smiley, David,Mayer, John P.,Gelfanov, Vasily M.,Perez-Tilve, Diego,Dimarchi, Richard D.,Pohl, Nicola L. B.,Liu, Fa. "Addition of Sialic Acid to Insulin Confers Superior Physical Properties and Bioequivalence". . p. 6134 - 6143. Retrieved 2020/07/10.