Orosz János Máté, Ujj Dóra, Kasal Petr, Benkovics Gábor, Bálint Erika
Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary.
Department of Organic Chemistry, Faculty of Science, Charles University, 128 43 Prague 2, Czech Republic.
Beilstein J Org Chem. 2023 Mar 9;19:294-302. doi: 10.3762/bjoc.19.25. eCollection 2023.
The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow conditions. After the optimization, the reaction steps were coupled in a semi-continuous flow system, since a solvent exchange had to be performed after the tosylation. However, the azidation and the reduction steps were compatible to be coupled in one flow system obtaining 6-monoamino-6-monodeoxy-β-cyclodextrin in a high yield. Our flow method developed is safer and faster than the batch approaches.
第一种连续流动法是为从天然β-环糊精开始，通过单甲苯磺酰化、叠氮化和还原三个反应步骤合成6-单氨基-6-单脱氧-β-环糊精而开发的。所有反应步骤均在连续流动条件下分别进行研究和优化。优化后，由于在甲苯磺酰化后必须进行溶剂交换，因此在半连续流动系统中耦合反应步骤。然而，叠氮化和还原步骤可以在一个流动系统中耦合，以高收率获得6-单氨基-6-单脱氧-β-环糊精。我们开发的流动方法比间歇法更安全、更快。
