Centrone Charla A, Lowary Todd L
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
J Org Chem. 2003 Oct 17;68(21):8115-9. doi: 10.1021/jo034475v.
An efficient method for the synthesis of glycosyl phosphinic acids (21) from the corresponding C-phosphonates is described. The route developed involves three steps: reduction of the glycosyl C-phosphonate to a primary phosphine, reaction of this product with an alkylating agent to afford a secondary phosphine, and finally oxidation to the phosphinic acid. Deprotection provides compounds suitable for testing as glycosyl phosphate analogues. Although the focus of this report is the synthesis of analogues of arabinofuranosyl-containing phosphate esters, the method should be readily applicable to other systems, carbohydrate or otherwise.
本文描述了一种从相应的C-膦酸酯合成糖基次膦酸（21）的有效方法。所开发的路线包括三个步骤：将糖基C-膦酸酯还原为伯膦，该产物与烷基化剂反应得到仲膦，最后氧化为次膦酸。脱保护得到适合作为磷酸糖类似物进行测试的化合物。尽管本报告的重点是含阿拉伯呋喃糖基磷酸酯类似物的合成，但该方法应易于应用于其他体系，无论是碳水化合物体系还是其他体系。
