稀有L-糖氟苷的合成

Synthesis of Rare L-Glycosyl F Luorides

本文采用"头尾翻转"策略,发展了一种通过烷氧自由基β-裂解(AOF)氟化反应,制备稀有L-糖氟苷的方法。通过容易制备的(-D-糖碳苷,选择性裸露伯羟基,再经二价银介导的AOF氟化反应制备了L-葡萄八碳糖氟苷,L-甘露八碳糖氟苷,L-来苏糖氟苷,5-氰基-L-来苏糖氟苷,为稀有L-糖氟苷的制备提供了新思路。

A convenient approach to synthesize rare L-glycosyl fluorides was achieved by merging AOF fluorination and head-to-tail inversion. Resorting to Ag(II) mediated AOF fluorination of 6-free hydroxyl of C-glycosides, we have successfully prepared L-gluco-octopyranosyl fluoride 3 a, L-manno-octopyranosyl fluoride 3 b, L-lyxopyranosyl fluoride 3 d and 6-deoxyl-6-amino-L-mannosyl fluoride 6, thus providing a new method to obtain rare L-glycosyl fluorides.