%0 Journal Article %J Tetrahedron %D 2012 %T Elaboration of the ether cleaving ability and selectivity of the classical pearlman's catalyst [Pd(OH)(2)/C]: concise synthesis of a precursor for a myo-inositol pyrophosphate %A Mart, Alson %A Shashidhar, Mysore S. %K Cyclitol %K Ether cleavage %K Inositol %K Palladium %K Protecting group %X

The cleavage of propargyl, allyl, benzyl, and PMB ethers by Pd(OH)(2)/C can be tuned in that order, by varying the reaction conditions. Other moieties such as C-C double bonds, esters, trityl ether, p-bromo and p-nitrobenzyl ethers are stable to these reaction conditions. Cleavage of allyl ethers can be made catalytic by using 1:1 mixture of Pd(OH)(2)/C and Pd/C. The synthetic potential of the selective ether cleaving ability of Pd(OH)(2)/C, essentially under neutral conditions, has been demonstrated by an efficient synthesis of a precursor for the preparation of an inositol pyrophosphate derivative. (C) 2012 Elsevier Ltd. All rights reserved.

%B Tetrahedron %I PERGAMON-ELSEVIER SCIENCE LTD %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %V 68 %P 9769-9776 %8 NOV %G eng %N 47 %3 Foreign %4 2.803 %R 10.1016/j.tet.2012.09.016