Abstract
ABSTRACT A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2'-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylchlorotin hydroxide 7, dibutyltin oxide 8, bis(dibutylchlorotin) oxide 10, its hydroxy congener 12, and tributyltin chloride 14 were also effective in a substoichiometric amount for the 2'-O-tosylation of the nucleoside 2. The method was applicable to some methyl glycopyranosides. The tosylation with tin dichloride 1 was not sensitive to the presence of water in the reaction mixture. Possible reaction pathways are discussed.
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