One-step, stereocontrolled synthesis of glycosyl 1-phosphates, uriidine-5'-diphosphogalactose, and uriidine-5'-diphosphoglucose from unprotected glycosyl donors

Research was conducted to examine a practical synthesis of O-glycosides using 2-(beta-D-glycosylocy)-3-methoxypyridine (MOP) donors. 1-phosphate esters of alpha-D-glucopyranose, alpha-D-galactopyranose and 2-azido-2-deoxy-alpha-D-galactopyranose were prepared without the need for protective groups since the reaction of MOP glycosides with phosphoric acid results in excellent stereoselectivity and the corresponding 1,2-cis-1-phosphates in good yield. Results demonstrate that MOP donors are versatile intermediates for the one-step stereocontrolled synthesis.