Reaction of 1,2-orthoesters with HF-pyridine: a method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis.

Glycosyl fluorides can be prepared in an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.