Novel 3-O-α-L-cladinosyl sixteen-membered macrolide antibacterials

Abstract

A novel series of 3-O-α-L-cladinosyl sixteen-membered macrolide antibacterials has been synthesized by glycosidation of the 3-hydroxy group of 12,13-de-epoxy-12,13-didehydrorosaramicin, 12,13-de-epoxy-12,13-didehydro-20-deoxorosaramicin, desmycosin, 20-deoxodesmycosin, and 19-deformyldesmycosin. The glycosidation was effected by reaction of the suitably protected macrolide substrates with the 1-S-pyridyl derivative of L-cladinose in the presence of either anhydrous silver perchlorate or anhydrous silver trifluoromethanesulphonate to afford the 3-O-α-glycosides in good yield.