Synthesis and structure of novel iodinated N-glycosyl-sulfonamides through Aza-Ferrier reaction of 2-substituted glycals

Abstract

We obtained a series of novel N-(2-iodo-2,3-dideoxy-2-en-glycopyranosides)-sulfonamides via the Aza-Ferrier rearrangement of protected-2-iodoglycals in good yields and high stereoselectivity. Their structure and conformation features were determined by NMR. Moreover, we report here the first in detail structure analysis by X-ray diffraction techniques of a 2-iodo-pseudoglycal.