Premium
Synthesis of the Mannopeptimycin Disaccharide and Its Conjugation with 4‐Alkylidene‐β‐lactams
Author(s) -
Adinolfi Matteo,
Giacomini Daria,
Iadonisi Alfonso,
Quintavalla Arianna,
Valerio Silvia
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701159
Subject(s) - chemistry , disaccharide , moiety , stereochemistry , reactivity (psychology) , acceptor , combinatorial chemistry , medicine , physics , alternative medicine , pathology , condensed matter physics
The disaccharide moiety of the antibiotic mannopeptimycin has been synthesized as a ( N ‐phenyl)trifluoroacetimidate donor, the reactivity of which was tested in conjugation with a 4‐alkylidene‐β‐lactam acceptor. Key steps of the synthesis were Bi(OTf) 3 ‐catalyzed glycosidations that proceeded in short times and with high yields and stereocontrol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)