Phillips M L, Bonjouklian R
Carbohydr Res. 1986 Jan 15;146(1):89-96. doi: 10.1016/0008-6215(86)85026-1.
A method for the synthesis of chiral cyclic analogues of platelet-activating factor (PAF) is reported. Treatment of suitably substituted derivatives of 2-deoxy-D-erythro-pentose with phosphorus oxychloride, followed by choline p-toluenesulfonate generates cyclic phospholipids in good yield. Further chemical modification produces other compounds including optically active gamma-butyrolactones such as 2-deoxy-5-O-hexadecyl-3-O-phosphocholyl-D-erythro-pentono-1, 4-lactone and 2-deoxy-3-O-hexadecyl-5-O-phosphocholyl-D-erythro-pentono-1, 4-lactone. All phospholipids were poor antagonists of PAF-induced aggregation of human platelets, and two analogs were poor agonists. The chemistry presented should be useful for the syntheses of other conformationally restricted analogues of PAF.
报道了一种合成血小板活化因子（PAF）手性环状类似物的方法。用三氯氧磷处理适当取代的2-脱氧-D-赤藓戊糖衍生物，然后用对甲苯磺酸胆碱处理，可高产率生成环状磷脂。进一步的化学修饰可产生其他化合物，包括光学活性的γ-丁内酯，如2-脱氧-5-O-十六烷基-3-O-磷酰胆碱基-D-赤藓戊糖-1,4-内酯和2-脱氧-3-O-十六烷基-5-O-磷酰胆碱基-D-赤藓戊糖-1,4-内酯。所有磷脂都是PAF诱导的人血小板聚集的弱拮抗剂，两种类似物是弱激动剂。所介绍的化学方法应有助于合成其他构象受限的PAF类似物。
