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

TitleElaboration 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
Publication TypeJournal Article
Year of Publication2012
AuthorsMart, A, Shashidhar, MS
JournalTetrahedron
Volume68
Issue47
Pagination9769-9776
Date PublishedNOV
ISSN0040-4020
KeywordsCyclitol, Ether cleavage, Inositol, Palladium, Protecting group
Abstract

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.

DOI10.1016/j.tet.2012.09.016
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.803
Divison category: 
Catalysis and Inorganic Chemistry
Organic Chemistry