The Journal of Organic Chemistry

Phospholipid synthesis based on new sequential phosphate and carboxylate ester bond formation steps

CJ Lacey, LM Loew

Index: Lacey, C. Jeffrey; Loew, Leslie M. Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5214 - 5221

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Citation Number: 12

Abstract

A total synthesis of racemic phosphatidylcholine is based on two novel but straightforward reaction sequences. The phosphate diester portion is constructed by successive displacement of the chlorines on methyl dichlorophosphate by allyl alcohol and dimethylethanolamine. The resulting triester isomerizes smoothly to allyl choline phosphate. The double bond is then converted to the bromohydrin to allow the sequential introduction ...