10.1021/acs.joc.9b02410
The research focuses on the development of a method for the stereoselective synthesis of aryl C-glycosides using the Matsuda-Heck arylation of glycals. The study explores the use of various arene diazonium salts as coupling partners with a deoxygenated glycal synthesized from L-ethyl lactate through a tandem RCM-isomerization sequence. Key chemicals involved in this research include the MOM-protected glycal L-amicetal, which serves as the starting material, and a range of arene diazonium salts with different substituents (such as methoxy, fluorine, chlorine, bromine, and hydroxyl groups) that undergo the coupling reaction with the glycal under optimized conditions. The products obtained can be further functionalized through hydrogenation, epoxidation, or dihydroxylation to yield various derivatives, including 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, and 6-desoxy aryl C-glycosides. The method is also applied to the synthesis of an α-configured 6-desoxy-gliflozin derivative, highlighting its potential for creating complex aryl C-glycoside structures with high hydrolytic and metabolic stability.