Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Org Lett. 2021 Apr 16;23(8):3216-3220. doi: 10.1021/acs.orglett.1c00969. Epub 2021 Apr 2.
We report a promoter-assisted glycosidation approach for the stereoselective synthesis of the 6-deoxy-β-d--heptopyranose oligosaccharides. SphosAuNTf-promoted glycosidation of 6-deoxy-d--heptopyranosyl -hexynylbenzoate with common alcohols afforded a range of 6-deoxy-d--heptosides with good to excellent β-selectivities. The counterion and the ligand of SPhosAuNTf were found to have a dramatic effect on the formation of the 1,2--β-linked 6-deoxy-d--heptosides. This approach was effectively applied to the stereocontrolled synthesis of the 6-deoxy-β-d--heptopyranose oligosaccharides relevant to and .
我们报告了一种促进剂辅助的糖苷化方法，用于立体选择性合成 6-去氧-β-D-庚吡喃糖寡糖。SphosAuNTf 促进的 6-去氧-d-庚吡喃糖基-己炔基苯甲酸酯与常见醇的糖苷化反应，得到了一系列具有良好至优异的β选择性的 6-去氧-d-庚糖苷。发现 SPhosAuNTf 的反离子和配体对 1,2-β-连接的 6-去氧-d-庚糖苷的形成有显著影响。该方法有效地应用于与 和 相关的 6-去氧-β-D-庚吡喃糖寡糖的立体控制合成。
