Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars.
Org Lett
; 19(16): 4403-4406, 2017 08 18.
Article
em En
| MEDLINE
| ID: mdl-28783355
ABSTRACT
An efficient one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycosides has versatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars. Under reagent-free conditions, the N-allyl-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furnished cyclopropane-fused iminosugars. The N-propargyl-C-nitromethyl glycosides underwent an unprecedented ketenimine-acrylamidine-Michael addition cascade reaction to give bicyclic amidines.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article