Zeidler J, Zimmermann W
Pharmazeutisches Institut, Universität Tübingen, Germany.
Chem Phys Lipids. 1994 Oct 20;74(1):73-81. doi: 10.1016/0009-3084(94)90113-9.
The synthesis of heterocyclic analogues of the platelet activating factor is described. The preparation starts with acylating rac-tetrahydro-1,3-thiazine-4-carboxylic acid ethyl ester, with palmitoyl chloride to form the amide linkage. Following ester reduction, the phosphocholine part is introduced via 2-chloro-2-oxo-1,3,2-dioxaphospholane and subsequent ring opening with trimethylamine under pressure. Furthermore, the related L-thiazolidine analogue is prepared using the same procedure. In addition the sulfinyl and sulfonyl derivatives of this compound are obtained by oxidation with 3-chloro-perbencoic acid. From one sulfinyl intermediate the diastereomeres are separated and their conformations are determinated by 13C-NMR spectroscopy.
描述了血小板活化因子杂环类似物的合成。制备过程从用棕榈酰氯酰化外消旋四氢-1,3-噻嗪-4-羧酸乙酯以形成酰胺键开始。酯还原后，通过2-氯-2-氧代-1,3,2-二氧磷杂环戊烷引入磷酸胆碱部分，并随后在压力下用三甲胺开环。此外，使用相同的程序制备相关的L-噻唑烷类似物。另外，该化合物的亚磺酰基和磺酰基衍生物通过用3-氯过苯甲酸氧化获得。从一种亚磺酰基中间体分离出非对映异构体，并通过13C-NMR光谱确定它们的构象。
