Issue 12, 2018

Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity

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 N6-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.

Graphical abstract: Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity

Supplementary files

Article information

Article type
Research Article
Submitted
10 Feb 2018
Accepted
09 May 2018
First published
11 May 2018

Org. Chem. Front., 2018,5, 1992-1999

Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity

T. Liu, Z. Zhu, H. Ren, Y. Chen, G. Chen, M. Cheng, D. Zhao, J. Shen, W. Zhu, B. Xiong and Y. Chen, Org. Chem. Front., 2018, 5, 1992 DOI: 10.1039/C8QO00165K

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