Synthesis of N,N'-Diacetyl-β-Chitobiosyl N-Glycooxazoline

The synthesis of N,N'-diacetyl-β-chitobiosyl N-glycooxazoline 2 was investigated. A routine method was used to prepare the N-benzyloxycarbonyl (Cbz) protected trichloroacetimidate donors 11 and 13. The synthesis was carried through using polystyrene as solid-phase support and o-nitrobenzyl ether tether as linker. The target compound 2 was efficiently obtained by iterative glycosylations, catalytic hydrogenation, acetylation, deacetylation, and photolysis.