Synthesis of Thio- and Selenophospholipids from 2,2,5,5-Tetra(hydroxymethyl)cyclopentanone

G. A. Savin^#

^# Phone (8442) 30-2896; e-mail: gasavin@mail.ru
Volgograd State Pedagogical University, pr. Lenina 27, Volgograd, 400131 Russia

Received December 30, 2005; in final form, March 14, 2006

Abstract: New phospholipids, thio- and selenoanalogues of phosphatidic acids, were synthesized on the basis of 2,2,5,5-tetra(hydroxymethyl)cyclopentanone. The starting tetraol monoketal was phosphorylated with amidophosphorous acid chlorides to protected polyol amidophosphites, which were further sulfurized or selenized to phosphoacetals. These were directly acylated with fatty acid chlorides to thio- and selenoanalogues of phospholipids.

Key words: amidophosphites, direct acylation of phosphoacetals, phosphites, phospholipid thio- and selenoanalogues, 2,2,5,5-tetra(hydroxymethyl)cyclopentanone

Russian Journal of Bioorganic Chemistry 2006, 32 (5):492-496