Publication: A versatile approach to the synthesis of glycans containing mannuronic acid residues
Issued Date
2021-03-28
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ISSN
14770520
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2-s2.0-85103508277
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Mahidol University
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.19, No.12 (2021), 2731-2743
Suggested Citation
Catherine Alex, Satsawat Visansirikul, Alexei V. Demchenko A versatile approach to the synthesis of glycans containing mannuronic acid residues. Organic and Biomolecular Chemistry. Vol.19, No.12 (2021), 2731-2743. doi:10.1039/d1ob00188d Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/76242
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Title
A versatile approach to the synthesis of glycans containing mannuronic acid residues
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Abstract
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 linkedviaβ-(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.