Monoalkylation of Tributyltin Activated Methyl 4,6-O-Benzylidene-α-D-gluco- and -galactopyranosides

Falguni Dasgupta; Per J. Garegg

doi:10.1055/s-1994-25649

Synthesis 1994; 1994(11): 1121-1123
DOI: 10.1055/s-1994-25649

short paper

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Monoalkylation of Tributyltin Activated Methyl 4,6-O-Benzylidene-α-D-gluco- and -galactopyranosides

Falguni Dasgupta^* , Per J. Garegg

^*Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, S-10691 Stockholm, Sweden

Abstract

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Monoalkylation of methyl 4,6-O-benzylidene-α-D-gluco- and galactopyranosides could be carried out in good yields using bis(tributyltin) oxide. Regioselectivity, giving predominant 2-substitution, was excellent in the case of D-glucopyranoside. The ratio of the tin reagent to that of the substrate seems to be critical in determining the yield and the extent of regioselectivity. Alkylation could also be carried out in solvents at a slower rate, using less reagent, but the regioselectivity was lower.

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