A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor).

Journal Article (Journal Article)

The synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine is described. An efficient alkylation procedure using (NaH/DMSO) catalysis is also described and applied to the synthetic scheme. The key intermediate 1-O-alkyl-2-(R)-O-benzyl-3-bromopropane was phosphonylated using tris(methylsilyl)phosphite; the resulting phosphonic acid was coupled to choline using trichloroacetonitrile/pyridine or triisopropylbenzenesulfonyl chloride/pyridine followed by catalytic hydrogenation to yield 1-O-alkyl-2(R)-hydroxypropane-3-phosphonocholine.

Full Text

Duke Authors

Cited Authors

  • Schmitt, JD; Nixon, AB; Emilsson, A; Daniel, LW; Wykle, RL

Published Date

  • October 1992

Published In

Volume / Issue

  • 62 / 3

Start / End Page

  • 263 - 268

PubMed ID

  • 1468125

International Standard Serial Number (ISSN)

  • 0009-3084

Digital Object Identifier (DOI)

  • 10.1016/0009-3084(92)90063-u

Language

  • eng

Conference Location

  • Ireland