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Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks

https://doi.org/10.1016/j.carres.2019.107900

Alex, Catherine ; Visansirikul, Satsawat ; Zhang, Yongzhen ; Yasomanee, Jagodige P. ; Codee, Jeroen ; Demchenko, Alexei V. ( February 2020 , Carbohydrate Research)

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Bromine‐Promoted Glycosidation of Conformationally Superarmed Thioglycosides

https://doi.org/10.1002/chem.201901969

Panza, Matteo ; Civera, Monica ; Yasomanee, Jagodige P. ; Belvisi, Laura ; Demchenko, Alexei V. ( August 2019 , Chemistry – A European Journal)

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Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides

https://doi.org/10.1016/j.carres.2018.09.003

Mannino, Michael P. ; Yasomanee, Jagodige P. ; Demchenko, Alexei V. ( December 2018 , Carbohydrate Research)

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Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

https://doi.org/10.1039/c8ob00477c

Wang, Tinghua ; Nigudkar, Swati S. ; Yasomanee, Jagodige P. ; Rath, Nigam P. ; Stine, Keith J. ; Demchenko, Alexei V. ( January 2018 , Organic & Biomolecular Chemistry)
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In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra- O -acetyl-α- d -glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.
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