Huonnic Kler, Linclau Bruno
School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK.
Department of Organic and Macromolecular Chemistry, Ghent University, Ghent 9000, Belgium.
Chem Commun (Camb). 2023 Jul 20;59(59):9082-9085. doi: 10.1039/d3cc02518g.
The acid-catalysed formation of glycosidic bonds is more difficult when glycosyl donors are fluorinated, especially at the 2-position. Here we report high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation in moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, illustrated with the synthesis of a pentafluorinated disaccharide.
当糖基供体被氟化时，尤其是在2-位，酸催化的糖苷键形成更加困难。在此，我们报道了在常规三氯乙酰亚胺酯/三甲基硅基三氟甲磺酸酯活化下，2,3-二氟和2,3,4-三氟葡萄糖和半乳糖吡喃糖苷供体与各种受体的高产率糖苷化和糖基化反应，其端基异构选择性为中等到高度。该方法能够合成高度氟化的聚糖，以一种五氟二糖的合成为例进行了说明。
