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Claisen-Ireland rearrangement: a new route to C-glycosides

✍ Scribed by Thierry Vidal; Arnaud Haudrechy; Yves Langlois

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 267 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01055-2

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✦ Synopsis

A Claisen-Ireland rearrangement led to the formation of C-glycan derivatives. Azidonitration-reduction or dihydroxylation afforded gluco-and galacto-derived [3-C-glycosides. Subsequent deprotonation of bicyclic lactones 16 allowed the control of the newly created asymmetric centre.

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