Article
No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues
Journal of Organic Chemistry
(2022)
Abstract
A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3-O-picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3-O-benzoylated donors is also reported.
Keywords
- Ethyl groups,
- Free radicals,
- Carbohydrates,
- Mixtures,
- Aromatic compounds Go to The Journal of Organic Chemistry
Disciplines
Publication Date
2022
DOI
10.1021/acs.joc.1c02351
Citation Information
Catherine Alex and Alexei Demchenko. "No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues" Journal of Organic Chemistry Vol. 87 Iss. 1 (2022) p. 271 - 280 Available at: http://works.bepress.com/alexei-demchenko/180/