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Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block

Dimitriou, Eleni; Miller, Gavin

Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block Thumbnail


Authors

Eleni Dimitriou



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.

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

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