The iodosulfonamidation of peracetylated glycals revisited: access to 1,2-di-nitrogenated sugars

Abstract

Iodosulfonamidation of peracetylated glycals was investigated using either a combination of N-iodosuccinimide/iodine or iodine chloride as a source of iodonium ion. 1,2-trans- and 1,2-cis-2-deoxy-2-iodo-1-sulfonamido hexoses were, respectively, obtained depending on the reagent system used. Both series of isomers were successfully converted to 1,2-di-nitrogenated compounds, for example, 1-azido-1,2-dideoxy-2-sulfonamido sugars, which are useful intermediates for the synthesis of N-linked glycoproteins or glycoconjugates.