One-pot synthesis of organophosphate monoesters from alcohols

Author(s)

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

Affiliation

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

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

• Document type: Journal article
• Source: Tetrahedron Letters; v. 54, n. 13, p. 1690-1692, MAR 27 2013.
• Web of Science Citations: 13

Abstract

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)

• FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
• Grantee: Ronaldo Aloise Pilli
• Support Opportunities: Research Projects - Thematic Grants