Abstract

Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described .This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.

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