The Journal of Organic Chemistry

An efficient stereocontrolled route to both enantiomers of platelet activating factor and analogs with long-chain esters at C-2: saturated and unsaturated ether …

PN Guivisdalsky, R Bittman

Index: Guivisdalsky, Pedro N.; Bittman, Robert Journal of Organic Chemistry, 1989 , vol. 54, # 19 p. 4643 - 4648

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Citation Number: 43

Abstract

Both enantiomers of various etherlester glycerophosphocholines (R)-and (S)-l, including platelet activating factor (PAF, 2), have been synthesized from arenesulfonate derivatives of glycidol ((R)-and (S)-3) that are readily available in high enantiomeric purity. Regio-and stereospecific opening of (R)-or (S)-3 with 1.0-1.4 equiv of long-chain saturated or unsaturated alcohol using boron trifluoride etherate as catalyst in CH2C12 or CHCl, ...