Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.
Org Biomol Chem. 2020 Mar 25;18(12):2242-2251. doi: 10.1039/d0ob00247j.
An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.
描述了一种高效的钯(ii)介导的糖苷与二芳基碘鎓盐的 C-糖苷化反应，为合成具有优异立体选择性的 2,3-二脱氧 C-芳基糖苷提供了一种新策略。该 C-糖苷化反应可以有效地对多种糖苷进行反应，包括 D-葡萄糖醛酸、D-半乳糖醛酸、D-allo 醛糖、L-鼠李糖醛酸、L-岩藻糖醛酸、L-阿拉伯糖醛酸、D-麦芽糖醛酸和 D-乳糖醛酸，并且可以获得中等至良好收率的相应 C-糖苷。由于该反应具有丰富的官能团相容性、广泛的底物范围和出色的α-立体选择性，因此该方法被认为是碳水化合物化学领域的一项重要进展。
