Synthesis of a Ring‐Rigid Disaccharide Model for Studies of Alkaline Chain Cleavage in Cellulose#

Abstract

2,6‐Anhydro‐1,3‐O‐methylene‐5‐O‐(4,6‐O‐methylene‐β‐D‐glucopyranosyl)‐D‐glycero‐D‐gulitol (1) was synthesized as a non‐reducing cellulose model compound for studying high temperature alkaline cleavage of the glucosidic linkage. The pyranoid rings of 1 are limited in their ability to change conformation by the methylene moieties attached to each ring. Thus the compound more closely models the situation for internal glycosidic linkages of cellulose. A related model with the 2′ hydroxyl group etherified, 2,6‐anhydro‐1,3‐O‐methylene‐5‐O‐(2‐O‐methyl‐4,6‐O‐methylene‐β‐D‐glucopyranosyl)‐D‐glycero‐D‐gulitol (2) was also synthesized. #Alkaline Degradation of Glycosides. Part 5.