Synthesis of Selectively Fully Protected Glucose Derivatives via a Furanose-to-Pyranose Rearrangement Method

Abstract

Towards the total synthesis of a natural anti-inflammatory compound present in the plant Sclerochloa dura, three full protection strategies were developed for selectively full protected glucose derivatives, available for subsequent 1,3,6- functionalization. Difficulty of distinguishing secondary carbohydrate hydroxyls for 3-O protection was overcome by employing a furanose-to-pyranose rearrangement method, affording allyl 3-O-benzyl-D-glucopyranoside. The three protection strategies were based on this shared intermediate.