Selective allylation of sugar derivatives containing the 1,1,3,3‐tetraisopropyldisiloxane‐1,3‐diyl protective group

Abstract

Abstract Using the method of Guibe et al. we were able to selectively introduce an allyl group at the 2‐position in methyl‐4,6‐ O ‐(tetraisopropyldisiloxane‐1,3‐diyl)‐α‐D‐glucopyranoside and benzyl‐4,6‐ O ‐(tetraisopropyldisiloxane‐1,3‐diyl)‐β‐D‐glucopyranoside. The dynamic properties of the tetraisopropyldisiloxane‐1,3‐diyl protective group gave us access to a glucose derivative which carried a 1‐propenyl group at the 2‐position, an allyl group at the 6‐position and a tetraisopropyldisiloxane‐1,3‐diyl at the 3,4‐position together with a glucose derivative protected with an allyl, an acetyl and a 3‐hydroxytetraisopropyldisiloxanyl at the 2‐, 3‐ and 4‐positions, respectively.