Glycosylations of Glycals using <i>N</i>‑Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2‑Iodo- and 2‑Deoxyglycosides

Abstract

The glycosylations of glycals and alcohols using <i>N</i>-iodosuccinimide (NIS) and a catalytic amount of PPh₃ effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh₃ significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P­(OPh)₃ were effectively realized to give the corresponding 2-deoxyglycosides in high yields