Microwave-Assisted Regioselective Benzylation: An Access to Glycal Derivatives with a Free Hydroxyl Group at C4

T Bieg, K Kral, J Paszkowska, W Szeja…

Index: Bieg, Tadeusz; Kral, Katarzyna; Paszkowska, Jadwiga; Szeja, Wiesaw; Wandzik, Ilona Journal of Carbohydrate Chemistry, 2012 , vol. 31, # 7 p. 593 - 601

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Citation Number: 3

Abstract

D-glucal, D-galactal, and their 6-O-TBDMS derivatives were benzylated in a two-step procedure under microwave conditions. In the first step glycals were converted into dibutylstannylene acetal or tributyltin ether intermediates, which were next alkylated with benzyl bromide in the presence of Bu4NBr. In all cases the 4-OH group stayed unsubstituted. Microwave-assisted benzylation contributes to a significant reduction of the ...

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