Synthesis of the C-glycoside analogue of a novel sialyl Lewis X mimetic.
Synthesis of the C-glycoside analogue of a novel sialyl Lewis X mimetic.
复制标题
新型唾液酸路易斯 X 模拟物的 C-糖苷类似物的合成。
DOI：
10.1021/jo991898h
复制
发表时间：
2000
期刊：
影响因子：
--
通讯作者：
Mootoo,DR
中科院分区：
文献类型：
--
作者：
Cheng,X;Khan,N;Mootoo,DR
唾液酸化刘易斯X（sLex）模拟物可作为选择素拮抗剂，在新型抗肿瘤治疗的开发中受到了相当大的关注。从Wong小组的研究中出现的一个有趣的结构是1，1-Gal-Man二聚体2，据报道其与E-选择素的结合强度是sLex的5倍。的C-糖苷衍生物3是作为选择素结合的构象探针和作为水解稳定的类似物的兴趣。在此，我们阐述了β-C-半乳糖-二糖合成3的一种新方法。该方案的关键步骤是新型氧碳正离子-烯醇醚环化，得到C1-取代的半乳糖醛。
Sialyl Lewis X (sLex) mimetics that can function as selectin antagonists have received considerable attention in connection with the development of novel antiinflammatory therapies. An interesting structure that emerged from the studies of the Wong group is the 1,1-Gal-Man disaccharide2, reported to bindE-selectin 5 times more strongly than sLex. TheC-glycoside derivative3is of interest both as a conformational probe for selectin binding and as a hydrolytically stable analogue. Herein we illustrate a novel methodology for β-C-galacto-disaccharides in the synthesis of3.The protocol has as a key step a novel oxocarbenium ion−enol ether cyclization to give a C1-substituted galactal.