Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides

Abstract

In an attempt to refine the H-bond-mediated Aglycone Delivery (HAD) glycosylation reaction reported herein is the synthesis of β-glucosides using an ethylthio glucoside donor equipped with the remote 6-O-picoloyl substituent. Upon examining various aliphatic, aromatic, and carbohydrate acceptors, it was determined that both electronic and steric factors may greatly affect the stereoselectivity of the HAD reaction with this donor.

Keywords: Glycosylation; Oligosaccharides; Stereoselectivity; Synthesis.