Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
by
Eleni Dimitriou and Gavin J. Miller *
Eleni Dimitriou and Gavin J. Miller *
Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire, ST5 5BG, UK
*
Author to whom correspondence should be addressed.
Molbank 2020, 2020(1), M1111; https://doi.org/10.3390/M1111
Received: 13 December 2019 / Revised: 14 January 2020 / Accepted: 16 January 2020 / Published: 18 January 2020
(This article belongs to the Special Issue Molecules from Side Reactions)
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.
Keywords:
glycosyl sulfoxide; uronate; thioglycoside oxidation; mannose
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Dimitriou, E.; Miller, G.J. Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank 2020, 2020, M1111.
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