Chiral Deuteration at C-5 of 1, 5-Anhydropentofuranose Derivatives

Abstract

Photobromination of 1, 5-anhydropentofuranoses and subsequent metal deuteride reduction of the resulting 5-exo-bromides gave C-5 chirally deuteratcd 1, 5-anhydropentofuranoses. The stereochemistry of the reduction is discussed in terms of the effects of substituents at C-2 and C-3 of 1, 5-anhydropento-furanoses.