One-pot synthesis of organophosphate monoesters from alcohols

Autor(es)

Lira, Lucas M. ^{[1, 2]} ; Vasilev, Dimitar ^[2] ; Pilli, Ronaldo A. ^[1] ; Wessjohann, Ludger A. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Leibniz Inst Plant Biochem, D-06120 Halle - Germany

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron Letters; v. 54, n. 13, p. 1690-1692, MAR 27 2013.
• Citações Web of Science: 13

Resumo

A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile. (c) 2013 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 09/51602-5 - Biologia química: novos alvos moleculares naturais e sintéticos contra o câncer, estudos estruturais, avaliação biológica e modo de ação
• Beneficiário: Ronaldo Aloise Pilli
• Linha de fomento: Auxílio à Pesquisa - Temático