Tetrahedron

The synthesis of isoprenoid (phosphinylmethyl) phosphonates

SA Biller, C Forster

Index: Biller, Scott A.; Forster, Cornelia Tetrahedron, 1990 , vol. 46, # 19 p. 6645 - 6658

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Citation Number: 46

Abstract

A synthetic route to isoprenoid (phosphinylmethyl) phosphonates (PMPs), stable analogues of the biologically important diphosphates, is described. This method involves the reaction of an α-phosphonate carbanion with an isoprenoid phosphonochloridate to provide the PMP triesters, followed by ester cleavage with TMSBr or TMSI. 13C NMR, 31P NMR, 19F NMR and FAB-MS data were employed for the characterization of PMP salts and triesters.