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Synlett 2014; 25(20): 2873-2878
DOI: 10.1055/s-0034-1379471
DOI: 10.1055/s-0034-1379471
letter
Exploring Glycosylation Reactions under Continuous-Flow Conditions
Weitere Informationen
Publikationsverlauf
Received: 25. Juni 2014
Accepted after revision: 16. September 2014
Publikationsdatum:
17. Oktober 2014 (online)
Abstract
The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.
Keywords
carbohydrates - glycosylation - flow chemistry - natural products - oligosaccharides - glycosidesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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