The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy- D -glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido- D -glucononitrile starting from D -glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy- D...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 68; no. 2; pp. 317 - 322
Main Authors Bird, P, Dolphin, D. H, Withers, S. G
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.02.1990
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Summary:The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy- D -glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido- D -glucononitrile starting from D -glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy- D -glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. Keywords: synthesis, amino-sugars, glycosidase inhibitors.
ISSN:0008-4042
1480-3291
DOI:10.1139/v90-045