Abstract

The solid-phase synthesis of allosamidin and its analogue di-N-acetyl-β-chitobiosyl NAG-thiazoline were investigated. The synthesis was performed using polystyrene as support and o-nitrobenzyl ether tether as linker. The target allosamidin 1 and di-N-acetyl-β-chitobiosyl N-acetylglucosamine (NAG)-thiazoline 2 were efficiently obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, deacetylation, and photolysis, respectively.

Keywords: Allosamidin and its analogue, glycosylation reactions, o-nitrobenzyl ether, solid-phase synthesis, N-acetylglucosamine, filtration, byproducts, organic synthesis, oxygen, chloride.