2-O-Methyl-b-D-N-acetylneuraminicacidmethylester

Base Information

• Chemical Name: 2-O-Methyl-b-D-N-acetylneuraminicacidmethylester
• CAS No.: 6730-43-4
• Molecular Formula: C13H23NO9
• Molecular Weight: 337.327
• Mol file: 6730-43-4.mol

Synonyms:2-O-Methyl--D-N-acetylneuraminic Acid, Methyl Ester

Chemical Property of 2-O-Methyl-b-D-N-acetylneuraminicacidmethylester

Chemical Property:

• Vapor Pressure: 4.32E-20mmHg at 25°C
• Melting Point: 115-125°C
• Refractive Index: 1.545
• Boiling Point: 657.7°C at 760 mmHg
• Flash Point: 351.6°C
• PSA: 154.78000
• Density: 1.41g/cm³
• LogP: -2.73840
• Solubility.: Hot Methanol, Water

Purity/Quality:

98%Min ^*data from raw suppliers

2-O-Methyl-β-D-N-acetylneuraminicAcid,MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-Methyl-b-D-N-acetylneuraminicacidmethylester

There total 55 articles about 2-O-Methyl-b-D-N-acetylneuraminicacidmethylester 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: 98.0%

(2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-2-methoxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (113974-12-2) → N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid (6730-43-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/ja00220a035

Reference yield: 93.0%

methanol (67-56-1) + N-acetyl neuraminic acid (19342-33-7) → N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid (6730-43-4)

Guidance literature:

With Amberlite IR-120 resin (H⁺form); for 48h; Reflux;

DOI:10.1021/ja405916q

Reference yield: 70.0%

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-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid (6730-43-4)

Guidance literature:

With Dowex H(+);

DOI:10.1016/S0040-4039(97)00237-2

upstream raw materials:

methanol

N-acetyl neuraminic acid

(2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-2-methoxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Benzoic acid (Z)-4-furan-2-yl-4-hydroxy-2-oxo-but-3-enyl ester

Downstream raw materials:

methyl -8,9-O-(thiocarbonyl)-β-D-glycero-D-galacto-2-nonulopyranosid>onate

Refernces

• 1、 Lifely, Robert M.,Cottee, Frank H.. "FORMATION AND IDENTIFICATION OF TWO NOVEL ANHYDRO COMPOUNDS OBTAINED BY METHANOLYSIS OF N-ACETYLNEURAMINIC ACID AND CARBOXYL-REDUCED, MENINGOCOCCAL B POLYSACCHARIDE". . p. 187 - 198. Retrieved 1982.
• 2、 Kim, Soong-Hoon,Constantine, Keith L.,Duke, Gerald J.,Goldfarb, Valentina,Hunt, John T.,Johnson, Stephen,Kish, Kevin,Klei, Herbert E.,McDonnell, Patricia A.,Metzler, William J.,Mueller, Luciano,Poss, Michael A.,Fairchild, Craig R.,Bhide, Rajeev S.. "Design, synthesis, functional and structural characterization of an inhibitor of N-acetylneuraminate-9-phosphate phosphatase: Observation of extensive dynamics in an enzyme/inhibitor complex". . p. 4107 - 4111. Retrieved 2013.
• 3、 Mertsch, Alexander,Poschenrieder, Silvan,Fessner, Wolf-Dieter. "Semi-Synthetic Sialic Acid Probes for Challenging the Substrate Promiscuity of Enzymes in the Sialoconjugation Pathway". supporting information. p. 5485 - 5495. Retrieved 2020/10/22.
• 4、 Buchini, Sabrina,Gallat, Francois-Xavier,Greig, Ian R.,Kim, Jin-Hyo,Wakatsuki, Soichi,Chavas, Leonard M. G.,Withers, Stephen G.. "Tuning mechanism-based inactivators of neuraminidases: Mechanistic and structural insights". supporting information. p. 3382 - 3386. Retrieved 2014/04/03.