Iodoamidation of Glycals: A Facile Preparation of 2‐Deoxy‐N‐glycosylamides

TLDR: 2-Deoxy-2-iodo-N-glycosylamides have been prepared in high yields and with good selectivities by a one step process starting from glycals by tin hydride mediated reductive deiodination.

Abstract: 2-Deoxy-2-iodo-N-glycosylamides have been prepared in high yields and with good selectivities by a one step process starting from glycals. The resulting trans-configured 2-deoxy-2-iodo-N-glycosylamides are readily converted to the 2-deoxy-N-glycosylamides by tin hydride mediated reductive deiodination. Aliphatic and aromatic primary amides, substituted ureas and amino acids were added to glycals in this fashion. The stereoselectivity and yields in these reactions were governed by a variety of factors including the nature of the solvent used in the addition reaction, the types of protecting groups on the glycal, and the nature of the R group on the amide.