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.
P. A. M. Herdewijn, A. Van Aerschot, L. Jie, E. Esmans, J. Feneau-Dupont and J. Declercq, J. Chem. Soc., Perkin Trans. 1, 1991, 1729 DOI: 10.1039/P19910001729
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