Regioselective Formation of Di-O-Benzyl-Substituted Hexopyranosides via Stannylene Acetal Intermediates

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Abstract
The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated. These reactions occur readily in benzyl bromide at 85 °C. At reaction times of one to two days, the major products are di-O-benzyl derivatives. In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70% yields, respectively. The species present in these reactions and the reaction pathway are discussed.

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