Caged compounds of a 2-deoxyglucose: Facile synthesis and their photoreactivity

An o-nitrobenzyl and an o-nitrophenethyl derivatized 2-deoxyglucose (caged 2-deoxyglucoses) were synthesized from 3,4,6-tri-O-acetyl-D-glucal in only two steps in moderate to good yields as isomeric mixtures, which were irradiated at 350 nm to afford a 2-deoxyglucose. Decomposition of the o-nitrophenethyl derivative upon photolysis proceeded more efficiently than that of the o-nitrobenzyl derivative.