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...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-07-01
|
| Series: | Molbank |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-8599/2017/3/M947 |
| _version_ | 1819056021202534400 |
|---|---|
| author | Laura Beswick Gavin J. Miller |
| author_facet | Laura Beswick Gavin J. Miller |
| author_sort | Laura Beswick |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-21T13:16:47Z |
| format | Article |
| id | doaj.art-19e0f93b782f4a8a83117aa9d1063b29 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-12-21T13:16:47Z |
| publishDate | 2017-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-19e0f93b782f4a8a83117aa9d1063b292022-12-21T19:02:42ZengMDPI 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 |
| 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 |
| title | 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_short | 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid |
| title_sort | 1 2 3 4 tetra o acetyl β d mannuronic acid |
| 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 |