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Toward Novel Glyconjugates: Efficient Synthesis of Glycosylated 4-Alkylidene--lactams

✍ Scribed by Matteo Adinolfi; Paola Galletti; Daria Giacomini; Alfonso Iadonisi; Arianna Quintavalla; Alessandra Ravidà

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 102 KB
Volume: 2006
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200500665

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✦ Synopsis

Abstract

A new class of glycoconjugated β‐lactams was accessed by direct glycosidation of a suitable 4‐alkylidene‐azetidin‐2‐one acceptor with several perbenzylated (N‐phenyl)trifluoroacetimidate donors activated by catalytic Yb(OTf)~3~. Goodstereocontrol was achieved by relying on the stereo directing effect of nitrile or ether solvents. Transfer hydrogenolysis under carefully controlled conditions enabled the removal of the benzyl group without affecting the β‐lactam double bond. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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