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Safe and scalable continuous flow azidophenylselenylation of galactal to prepare galactosamine building blocks

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Guberman,  Mónica
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pieber,  Bartholomäus
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Guberman, M., Pieber, B., & Seeberger, P. H. (2019). Safe and scalable continuous flow azidophenylselenylation of galactal to prepare galactosamine building blocks. Organic Process Research & Development, 23(12), 2764-2770. doi:10.1021/acs.oprd.9b00456.


Cite as: http://hdl.handle.net/21.11116/0000-0005-5984-2
Abstract
Differentially protected galactosamine building blocks are key components for the synthesis of human and bacterial oligosaccharides. The azidophenylselenylation of 3,4,6-tri-O-acetyl-d-galactal provides straightforward access to the corresponding 2-nitrogenated glycoside. Poor reproducibility and the use of azides that lead to the formation of potentially explosive and toxic species limit the scalability of this reaction and render it a bottleneck for carbohydrate synthesis. Here, we present a method for the safe, efficient, and reliable azidophenylselenylation of 3,4,6-tri-O-acetyl-d-galactal at room temperature, using continuous flow chemistry. Careful analysis of the transformation resulted in reaction conditions that produce minimal side products while the reaction time was reduced drastically when compared to batch reactions. The flow setup is readily scalable to process 5 mmol of galactal in 3 h, producing 1.2 mmol/h of product.