1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
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 us...
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MDPI AG
2017-07-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2017/3/M947 |
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doaj-19e0f93b782f4a8a83117aa9d1063b292020-11-25T00:10:10ZengMDPI AGMolbank1422-85992017-07-0120173M94710.3390/M947M9471,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic AcidLaura Beswick0Gavin J. Miller1Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire ST5 5BG, UKLennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire ST5 5BG, UK1,2,3,4-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.https://www.mdpi.com/1422-8599/2017/3/M947mannuronic aciduronateTEMPO/BAIBoxidationNMR |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Laura Beswick Gavin J. Miller |
| spellingShingle |
Laura Beswick Gavin J. Miller 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid Molbank mannuronic acid uronate TEMPO/BAIB oxidation NMR |
| author_facet |
Laura Beswick Gavin J. Miller |
| author_sort |
Laura Beswick |
| title |
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_short |
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_full |
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_fullStr |
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_full_unstemmed |
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_sort |
1,2,3,4-tetra-o-acetyl-β-d-mannuronic acid |
| publisher |
MDPI AG |
| series |
Molbank |
| issn |
1422-8599 |
| publishDate |
2017-07-01 |
| description |
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. |
| topic |
mannuronic acid uronate TEMPO/BAIB oxidation NMR |
| url |
https://www.mdpi.com/1422-8599/2017/3/M947 |
| work_keys_str_mv |
AT laurabeswick 1234tetraoacetylbdmannuronicacid AT gavinjmiller 1234tetraoacetylbdmannuronicacid |
| _version_ |
1725409052974907392 |