Rapid access to 6″-functionalized α-galactosyl ceramides by using 2-naphthylmethyl ether as the permanent protecting group.

ABSTRACT

A versatile strategy for the synthesis of 6″-functionalized α-GalCers by using NAP ether group for permanent hydroxyl protection was developed, which provide the flexibility necessary for the incorporation of a wide range of functional groups in target molecules including alkyne, azide, thiol that are intolerant to Pd-catalyzed hydrogenolysis as well as other functionalities like carboxylic acid and amine. This strategy is also adaptable to other glycoconjugate synthesis especially those containing clickable tags and unsaturated functionalities.