A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates

Article abstract of DOI:10.3987/com-95-s71

A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.