1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire ST5 5BG, UK
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Molbank 2017, 2017(3), M947; https://doi.org/10.3390/M947
Received: 3 July 2017 / Revised: 10 July 2017 / Accepted: 11 July 2017 / Published: 14 July 2017
(This article belongs to the Section Organic Synthesis)
1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target compound using TEMPO/BAIB. None of the synthetic steps required column chromatography and the product was fully characterized by 1H-NMR, 13C-NMR, 2D NMR, MS and IR.
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Keywords:
mannuronic acid; uronate; TEMPO/BAIB; oxidation; NMR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
- Supplementary File 1:
Molbank 3D structure (MOL, 2 KiB)
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3D structure generated by CORINA Classic by MN-AM. - Supplementary File 2:
Molbank (INCHI, 775 B)
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MDPI and ACS Style
Beswick, L.; Miller, G.J. 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid. Molbank 2017, 2017, M947. https://doi.org/10.3390/M947
AMA Style
Beswick L, Miller GJ. 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid. Molbank. 2017; 2017(3):M947. https://doi.org/10.3390/M947
Chicago/Turabian StyleBeswick, Laura; Miller, Gavin J. 2017. "1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid" Molbank 2017, no. 3: M947. https://doi.org/10.3390/M947
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