Stereoselective photochemical cyclization of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose derivatives

Photoirradiation of a solution of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose in benzene for 92 h gave (6S)-3,6-anhydro-1,2-O-isopropylidene-5-c-methyl-6-c-phenyl-α-D-gluco- and -β-L-idofuranose in 54% and 11% yield, respectively. Related photocyclizations and solvent effects in the reactions were also described.