Regioselective reductive openings of acetals; mechanistic details and synthesis of fluorescently labeled compounds

R Johnsson, K Mani, F Cheng…

Index: Johnsson, Richard; Mani, Katrin; Cheng, Fang; Ellervik, Ulf Journal of Organic Chemistry, 2006 , vol. 71, # 9 p. 3444 - 3451

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Citation Number: 13

Abstract

Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3⊙ NMe3- AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, antiproliferative activity, and ...