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J Org Chem. 2002 Jul 12;67(14):5009-10. doi: 10.1021/jo0258453.

Synthesis of (E)-4-hydroxydimethylallyl diphosphate. An intermediate in the methyl erythritol phosphate branch of the isoprenoid pathway.

The Journal of organic chemistry

David T Fox, C Dale Poulter

Affiliations

  1. Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.

PMID: 12098326 DOI: 10.1021/jo0258453

Abstract

The syntheses of (E)-1-hydroxy-2-methyl-2-buten-4-yl diphosphate ((E)-4-hydroxydimethylallyl diphosphate, HDMAPP), an intermediate in the methyl erythritol phosphate pathway, and (E)-[4-(2)H]HDMAPP were accomplished in two steps from (E)-4-chloro-2-methyl-2-butenal. The synthetic route is easily adaptable for the facile incorporation of tritium at C-4 of the diphosphate.

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