Radical-induced cyclization of the S-methyl dithiocarbonate of 1,2-O-isopropylidene-α-xylose
Abstract
Reaction of the 3,5-bis-(S-methyl dithiocarbonate) of 1,2-O-isopropylidene-α-D-xylose with tributyltin hydride gives not the expected 3-deoxygenated xylo-furanose but instead the 3-thio-α-D-xylo-furanose derivative 4 resulting from radical cyclization. The structure of compound 4 was confirmed by X-ray crystallography. The absolute configuration has been established.