Eleni Dimitriou
Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
Dimitriou, Eleni; Miller, Gavin
Abstract
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis.
Citation
Dimitriou, E., & Miller, G. (2020). Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank, 2020(1), M1111. https://doi.org/10.3390/M1111
Journal Article Type | Article |
---|---|
Acceptance Date | Jan 16, 2020 |
Online Publication Date | Jan 18, 2020 |
Publication Date | Jan 18, 2020 |
Journal | Molbank |
Publisher | MDPI |
Peer Reviewed | Peer Reviewed |
Volume | 2020 |
Issue | 1 |
Article Number | ARTN M1111 |
Pages | M1111 |
DOI | https://doi.org/10.3390/M1111 |
Keywords | glycosyl sulfoxide; uronate; thioglycoside oxidation; mannose |
Publisher URL | https://www.mdpi.com/1422-8599/2020/1/M1111 |
Files
molbank-2020-M1111-v2.pdf
(689 Kb)
PDF
Publisher Licence URL
https://creativecommons.org/licenses/by/4.0/
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