1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
by
Laura Beswick and Gavin J. Miller *
Laura Beswick 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 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.
View Full-Text
Keywords:
mannuronic acid; uronate; TEMPO/BAIB; oxidation; NMR
▼
Show Figures
Graphical abstract
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 KB)
Display in JSmol Viewer
3D structure generated by CORINA Classic by MN-AM. - Supplementary File 2:
Molbank (INCHI, 775 B)
- Supplementary File 3:
Molbank (MOL, 2 KB)
Display in JSmol Viewer
- Supplementary File 4:
Supplementary (PDF, 1431 KB)
MDPI and ACS Style
Beswick, L.; Miller, G.J. 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid. Molbank 2017, 2017, M947.
Show more citation formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.
