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A versatile approach to the synthesis of glycans containing mannuronic acid residues

https://doi.org/10.1039/D1OB00188D

Alex, Catherine ; Visansirikul, Satsawat ; Demchenko, Alexei V. ( April 2021 , Organic & Biomolecular Chemistry)
null (Ed.)
Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported.
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A versatile approach to the synthesis of mannosamine glycosides

https://doi.org/10.1039/D0OB01640C

Alex, Catherine ; Visansirikul, Satsawat ; Demchenko, Alexei V. ( September 2020 , Organic & Biomolecular Chemistry)
null (Ed.)
O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group.
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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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