SYNTHESE DE PHOSPHORAMIDATES DE 2-DESOXY-2-IODOGLYCOSYLES

Article abstract of DOI:10.1016/0008-6215(87)80057-5

Addition of iodoazide to acetylated, benzylated, and methoxymethylated glycals yielded 2-deoxy-2-iodoglycosyl azides with 1,2-trans configuration.Stereoselectivity of the reaction favored the manno and talo configurations starting from D-glucal and D-galactal, respectively.With D-xylal derivatives, the stereoselectivity depended on the nature of the substituents.The Staudinger reaction of 2-deoxy-2-iodoglycosyl azides with trimethylphosphite led to the corresponding 2-deoxy-iodoglycosyl phosphoramidates in high yield.