Continuous flow chemistry with automation has the potential to democratize access to small complex glycans.^[1] Some of the most commonly-used glycosyl donors include the trichloroacetimidates and the N-phenyl trifluoroacetimidates. ^[2-4] Herein, we present a two-step telescoped sequence for the synthesis of these glycosyl donors via automated continuous flow chemistry.^[5] The developed methods provide access to trichloroacetimidates and the N-phenyl trifluoroacetimidates glycosyl donors of various carbohydrate building blocks without requiring work-up or chromatographic purification post-synthesis. This new method provides an easy, quick, and easily scalable approach to producing these activated glycosyl donors from more stable building blocks.

References:
[1] Breen, C. P.; Nambiar, A. M. K.; Jamison, T. F.; and Jensen, K. F., Trends in Chemistry, 2021, 3, 373-386.
[2] Zhu, X.; and Schmidt, R. R. Angew. Chem., Int. Ed., 2009, 48, 1900-1934
[3] Yu, B.; and Sun, J. Chem. Commun. 2010, 46, 4668-4679.
[4] DeYong, A. E.; Rudich, M. L.; Pohl, N. L. B. 2.21 - Synthesis of Carbohydrate Building Blocks for Automated Oligosaccharide Construction. In Comprehensive Glycoscience (Second Edition); Barchi, J. J., Ed.; Elsevier: Oxford, 2021; pp 637–659.
[5] Yalamanchili, S.; Nguyen, T.-A.; Zsikla, A.; Stamper, G.; DeYong, A. E.; Florek, J.; Vasquez, O.; Pohl, N. L. B.; Bennett, C. S. Angew. Chem. Int. Ed. 2021, 60, 23171–23175

Meenakshi Singh

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