Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate

Wootton, Hannah S.; J. Miller, Gavin

Abstract

Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH3.THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The resultant uronic acid was esterified with either a methyl or benzyl moiety. The products were obtained on a multigram scale and fully characterised by 1H, 13C and 2D NMR, alongside MS and IR analysis.

Citation

Wootton, H. S., & J. Miller, G. (2024). Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate. Molbank, 2024(3), Article M1847. https://doi.org/10.3390/M1847

• Journal Article Type: Article
• Acceptance Date: Jul 5, 2024
• Online Publication Date: Jul 9, 2024
• Publication Date: 2024-07
• Deposit Date: Aug 8, 2024
• Journal: Molbank
• Publisher: MDPI
• Peer Reviewed: Peer Reviewed
• Volume: 2024
• Issue: 3
• Article Number: M1847
• DOI: https://doi.org/10.3390/M1847
• Keywords: glucuronic acid; TEMPO; regioselective; oxidation; NMR
• Public URL: https://keele-repository.worktribe.com/output/878273
• Publisher URL: https://www.mdpi.com/1422-8599/2024/3/M1847