Heptose, 3-acetamido-3-deoxy

The simple and well-established behavior of alditol acetates upon electron impact makes these derivatives suitable for identification of sugars. Thus, tetroses, pentoses, hexoses, and heptoses give characteristic spectra that can be fully interpreted. The presence and positions of deoxy groups or acetamido functions can readily be determined. Ambiguities... 

Reaction of 3-acetamido-3-deoxy-4,5 6,7-di-0-isopropylidene-2-0-methyl-a/dle/i> dlo-D-g/yccro-D-gfl/flcro-heptose with [ethoxy(ethoxycarbonyl)methylene]-triphenyl-phosphorane, followed by an ethoxymercuration-demercuration reaction and acid hydrolysis resulted in the formation of the ethyl esters of 4-0-methyl-N-acetylneuraminic acid and 4-0-methyl-4-epi-N-acetylneuraminic acid (Beau et al. 1978). By oxymercuration of ethyl 5-acetamido-3,5-dideoxy-2-0-ethyl-4-0-methyl-D-g/jcero-D-ga/acto-non-2-enonate with mercury(II) trifluoroacetate, followed by borohydride-demercuration, 4-0-methyl-N-acetylneuraminic acid ethyl (3-glycoside was obtained (Beau et al. 1980). 4-0-Methyl-N-acetylneuraminic acid has been used in metabolism studies, as reported by Beau and Schauer (1980). Using tritiated sodiumborohydride, the corresponding 4-0-methyl-N-acetyl-[3-3H]neuraminic acid was obtained (Beau and Schauer 1980). 

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