Application of NAP ether-mediated intramolecular aglycon delivery to stereoselective construction of xylomannan fragment containing 1,2-cis glycosides

摘要

The methodology toward the strereoselective 1,2-cis-glycoside using 2-naphthylmethyl (NAP) ether-mediated intramolecular aglycon derivery (IAD) has been developed [1]. C2-O NAP-protected donors were cleanly converted to the mixed acetal upon oxidative activation with DDQ. Subsequent activation of thioglycosidic linkage initiated the rearrangement of an aglycon from 2-naphthylidene acetal moiety to give a desired 1,2-cis-glycoside with complete stereoselectivity.