In condensation reactions of 2,3,5-tri-O-benzoyl-d-ribofuranosyl acetate with various kinds of enol silyl ethers in the presence of tin(IV) chloride, the acetate behaves as an ambident electrophile to give two types of products arising from nucleophilic attack of the enol ether on C-1 carbon of the ribose derivative and on carbonyl carbon of 2-benzoyloxyl group, depending remarkably on the enol silyl ethers.
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Yokoyama et al. (1984) studied this question.
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