117193-44-9

Basic information

• Product Name: N-acetyl-4,7-dideoxyneuraminic acid
• Synonyms: N-acetyl-4,7-dideoxyneuraminic acid
• CAS NO: 117193-44-9
• Molecular Formula: C11H19NO7
• Molecular Weight: 277.27106
• Mol File: 117193-44-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 659.4°Cat760mmHg
• Flash Point: 352.6°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 3.45E-20mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: N-acetyl-4,7-dideoxyneuraminic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-acetyl-4,7-dideoxyneuraminic acid(117193-44-9)
• EPA Substance Registry System: N-acetyl-4,7-dideoxyneuraminic acid(117193-44-9)

Safety Data

• Hazardous Substances Data: 117193-44-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H19NO7/c1-6(14)12-8-2-3-11(18,10(16)17)19-9(8)4-7(15)5-13/h7-9,13,15,18H,2-5H2,1H3,(H,12,14)(H,16,17)/t7?,8-,9+,11-/m0/s1

Upstream product

• 117193-42-7 Methyl-5-acetamido-3,5-didesoxy-4,7-di-O-(methyldithiocarboxy)-8,9-(methylethyliden)-β-D-glycero-D-galakto-2-nonulopyranosidonsaeuremethylester 
• 88481-35-0 Methyl-5-(acetylamino)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 

Relevant articles and documents

Structural Transformations of N-Acetylneuraminic Acid, VIII. Synthesis of 7-, 8-, 9-Deoxy- and 4,7-Dideoxyneuraminic Acid

The 7- and 8-Iodnonulosonic acid derivatives 1 and 2 react with tributyltinhydride-AIBN to the 7- and 8-deoxy-N-acetylneuraminic acid derivatives 3a and 4a which after hydrolysis give the 7-deoxy-N-acetylneuraminic acid 3b (5-N-acetamido-3,5,7-trideoxy-β-D-galacto-2-nonulopyranosidonic acid = 7-Deoxy-Neu5Ac) and 8-deoxy-N-acetylneuraminic acid 4b (5-N-acetamido-3,5,8-trideoxy-β-D-galacto-2-nonulopyranosidonic acid = 8-Deoxy-Neu5Ac).The 4,8,9-tris-(t-butyldimethylsilyl)-N-acetylneuraminic acid derivative 5a yields after transformation to the 7-O-acetyl compound 5b and partial removing of the protecting groups the derivative 5c.Further reaction with the Mitsunobu-reagent and methyliodide affords the 9-Iodocompound 6a which turned to the 8-O-acetylderivative 6b.Subsequent reduction by means of tributyltinhydride yields first the 9-deoxyderivative 7a and after hydrolysis the 9-deoxy-N-acetylneuraminic acid 7b (5-N-acetyl amido-3,5,9-trideoxy-D-glycero-β-d-galacto-2-nonulopyranosidonic acid = 9-Deoxy-Neu5Ac).Another synthesis of 7b follows the route 8f -> 8g -> 7c.The Deoxy-N-acetylneuraminic acid 3b could be prepared also by an alternative procedure using the methyl-β-8,9-methylethylen-4-O-t-butyldimethylsilyl-N-acetylneuraminic acid methylester 8a via the intermediate compounds 8d and 8e.Application of the 8,9-O-methylethyliden-N-acetylneuraminic acid derivative 8 opens an approach to the xanthogenates 8a and 8b which could be reduced to the deoxy-N-acetylneuramic acid derivatives 9a and 10a.Hydrolysis of 10a yields the 4,7-dideoxy-N-acetylneuraminic acid 10b (5-N-acetamido-3,4,5,7-tetradeoxy-β-D-lyxo-2-nonulopyranosidonic acid = 4,7-Dideoxy-Neu5Ac). - Keywords: Deoxygenation of sialic acids; Xanthogenates of sialic acids; Reaction of side chain deoxy-iodo sialic acid with tributyltinhydride; Reaction of xanthogenates of sialic acids derivatives with tributyltinhydrde