A new synthesis of lysophosphatidylcholines and related derivatives. Use of p-toluenesulfonate for hydroxyl group protection
R Rosseto, N Bibak, R DeOcampo, T Shah…
Index: Rosseto, Renato; Bibak, Niloufar; DeOcampo, Rosemarie; Shah, Trishul; Gabrielian, Ara; Hajdu, Joseph Journal of Organic Chemistry, 2007 , vol. 72, # 5 p. 1691 - 1698
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Citation Number: 12
Abstract
A new stereoselective synthesis of lysophosphatidylcholines is reported. The synthesis is based upon (1) the use of 3-p-toluenesulfonyl-sn-glycerol to provide the stereocenter for construction of the optically active lysophospholipid molecule,(2) tetrahydropyranylation of the secondary alcohol function to achieve orthogonal protection of the sn-2-and sn-3- glycerol positions, and (3) elaboration of the phosphodiester headgroup using a 2-chloro- ...
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