Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity12. Issue 12 (16th May 2018)

• Record Type: Journal Article
• Authors: Liu, Tongchao; Zhu, Zhengdan; Ren, Huanming; Chen, Yabin; Chen, Guohua; Cheng, Maosheng; Zhao, Dongmei; Shen, Jingkang; Zhu, Weiliang; Xiong, Bing; Chen, Yue-Lei
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 12(2018)
• Page Start: 1992
• Page End: 1999
• Publication Date: 2018-05-16
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00165k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Valuable C -nucleosides are efficiently prepared with excellent anomeric selectivity depending on protecting groups on sugar moiety. Abstract : C -Nucleosides constitute a valuable class of compounds in biological and medicinal chemistry studies. We report herein a new and efficient synthesis of both alpha - and beta-C -nucleosides with high anomeric selectivity from N 6 -Boc protected purine analogues. The synthetic approach features a carefully designed lithiation and silane reduction sequence. The anomeric stereochemistry outcome is dictated by the protecting group of sugar lactones. Computational studies suggest that previously neglected interactions between partially positively-charged silane and the substitutions on a sugar moiety play important roles in the anomeric selectivity of silane-mediated C -nucleoside synthesis.