Publication: A versatile approach to the synthesis of mannosamine glycosides
Issued Date
2020-09-14
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ISSN
14770520
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2-s2.0-85090250795
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Mahidol University
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.18, No.34 (2020), 6682-6695
Suggested Citation
Catherine Alex, Satsawat Visansirikul, Alexei V. Demchenko A versatile approach to the synthesis of mannosamine glycosides. Organic and Biomolecular Chemistry. Vol.18, No.34 (2020), 6682-6695. doi:10.1039/d0ob01640c Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/58955
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Title
A versatile approach to the synthesis of mannosamine glycosides
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Abstract
© The Royal Society of Chemistry. 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. This journal is