ABSTRACT

In the first part of this review, recent results of the anomericO-alkylation procedure for glycoside bond formation will be discussed, with particular emphasis on α-glycoside bond formation with KDO, anomericO-alkylation of partially or completely unprotected sugars, and on results with alkylating agents derived from secondary hydroxy groups of sugars. The second part is devoted to the trichloroacetimidate method displaying recent applications to glycosphingolipid, glycopeptide, glycopeptidolipid, saponin, and antibiotics syntheses. Additionally, methodological improvements such as the “inverse procedure”, the “nitrile effect”, and die extension to partiallyO-protectedO-glycosyl trichloroacetimidates are discussed. In the last section, other anomeric oxygen activation procedures are briefly discussed.