Yalamanchili Subbarao, Nguyen Tu-Anh V, Pohl Nicola L B, Bennett Clay S
Department of Chemistry, Tufts University, 62 Talbot Ave, Medford, MA 02145, USA.
Department of Chemistry, Indiana University, 212 S. Hawthorne Dr, Bloomington, IN, 47405, USA.
Org Biomol Chem. 2020 May 6;18(17):3254-3257. doi: 10.1039/d0ob00522c.
An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to prevent unwanted exotherms and required shorter reaction times.
本文描述了一种高效、模块化的连续流动过程，用于制备两种正交保护的糖烯，并开发了几种常见保护基团在流动体系中加成的反应条件，包括苄基、萘甲基和叔丁基二甲基硅基醚的加成。该过程仅需21 - 37分钟的流动时间，就能以57 - 74%的总收率得到所需的目标化合物。此外，与间歇反应条件不同，连续流动过程无需主动冷却来防止不必要的放热，且反应时间更短。
