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On the Way to Glycoprocessing Inhibitors. Synthesis of an imidazo-L-xylo-piperidinose derivative

✍ Scribed by Andrzej Frankowski; Dariusz Deredas; Didier Le Nouen; Théophile Tschamber; Jacques Streith

Publisher: John Wiley and Sons
Year: 1995
Tongue: German
Weight: 352 KB
Volume: 78
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19950780717

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✦ Synopsis

Abstract

An eight‐step synthetic sequence led from the known D‐xylo‐pentodialdose 8 to imidazo‐L‐xylo‐piperidinose 15, the key steps being the build‐up of imidazole compound 12 by a van Leusen methodology and the intramolecular S~N~2 ring closure of the O‐triflated benzylidene derivative 13. xylo‐Piperidinose 15 appears in a half‐chair conformation like the oxocarbonium ions which are the postulated intermediates in the glycoprocessing of the pyranose polysaccharides. This bicyclic azasugar should be a glycosidase inhibitor.

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