Reaction of cyclic thioxocarbonates with tributyltin hydride.

Treatment of methyl 2-O-acetyl-3, 4-O-thiocarbonyl-β-L-arabinopyranoside with tributyltin hydride produced seven compounds, depending on the reaction conditions : the deoxy derivatives (2 and 3), the methylidene derivative (4), the carbonate (5), the O, S-rearrangement products (7 and 8), and the 4-deoxy acetyl migration product (9). Their structures were determined by spectroscopic and chemical means, and their formation mechanisms are discussed.