On the synthesis of C-glycosyl compounds containing double bonds without the use of protecting groups
作者:Günter Wulff、Guy Clarkson
DOI:10.1016/0008-6215(94)84109-8
日期:1994.4
Abstract A new range of C-glycosyl compounds carrying double bonds have been synthesised as potential monomers for the preparation of polyvinylsaccharides. The syntheses were performed without the use of protecting groups and mostly in water as solvent. The starting material was the easily accessible 5-β- d -glucopyranosyl-1,3-dimethylbarbituric acid sodium salt (3a) (obtained from d -glucose and 1
摘要合成了一系列带有双键的C-糖基化合物,作为制备多糖的潜在单体。在不使用保护基的情况下进行合成,并且大多数在水中作为溶剂。起始原料是易于获得的5-β-d-吡喃葡萄糖基-1,3-二甲基巴比妥酸钠盐(3a)(从d-葡萄糖和1,3-二甲基巴比妥酸水溶液中获得)。详细研究了巴比妥酸酯部分C-5处3a的烷基化反应。通过超声/相转移催化剂促进的烷基化,它可与Me2SO中的苄基溴和烯丙基或苄基溴一起很好地工作。生成的5,5-二烷基化的巴比妥酸酯5a-c和7a-c经历了巴比妥环异常灵活的裂解,失去了C-2羰基,