Stereoselective synthesis of α-glycosyl phosphites and phosphoramidites via o-selective glycosylation of H-phosphonate derivatives

Article abstract of DOI:10.1021/ol802190x

(Chemical Equation Presented) A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I^- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various α-glycosyl phosphites and phosphoramidites In a highly stereoselective manner with complete O-selectivity.