Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

Carsten Schultz; Thomas Metschies; Benjamin Gerlach; Christoph Stadler; Bernd Jastorff

doi:10.1055/s-1990-21022

Synlett 1990; 1990(3): 163-165
DOI: 10.1055/s-1990-21022

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Regioselective Synthesis of Inositol Phosphate Diesters via a Cyclic Phosphate Triester Approach

Carsten Schultz^* , Thomas Metschies, Benjamin Gerlach, Christoph Stadler, Bernd Jastorff

^*Institut für Organische Chemie, Universität Bremen, D-2800 Bremen 33, Federal Republic of Germany

Abstract

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Phosphate-substituted analogues of myo-inositol 1-phosphate and 2-phosphate were synthesized by a novel method via a five-membered cyclic phosphate triester intermediate, which was cleaved regioselectively by various alcohols. Low temperatures and bulky alcohols gave higher selectivity for myo-inositol 1-phosphate alkyl esters. Addition of sodium sulfite to the reaction mixture yielded predominantly the 2-phosphate diester.

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