A route to 3-deoxy-4-O-methyl-D-manno-oct-2-ulosonic acid (4-O-methyl-KDO) and its D-gluco isomer derivatives
โ Scribed by Zbigniew Pakulski; Aleksander Zamojski
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 377 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
โฆ Synopsis
Methoxymercuration of ~ fl-unsaturated ketoester 5 (readily obtained from peracetylated Dgluconic acid 1 via Barton ester) led to a separable mixture of KDO derivative 9 and its D-gluco isomer 10.
๐ SIMILAR VOLUMES
Treatment of methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-cr-D-manno-oct-2ulopyranosonic acid, or its methyl ester, with refluxing methanolic O.lM hydrogen chloride for 16 h gave 95% of methyl (methyl 3-deoxy-a-D-manno-act-2-ulopyranosid)onate. Acetylation of the methyl ester of 3-deoxy-D-manno-act-2ulo
Treatment of 2,3:5,6-di-0-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate. Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4
Benzyl 2-acetamido-2-deoxy-3-O-methyl-alpha-D-glucopyranoside (3) was obtained by deacetalation of its 4,6-O-benzylidene derivative (2). Compound 2 was prepared by methylation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside with methyl iodide-silver oxide in N,N-dimethylforma
3Deoxy-D-manno-2-octulosonic acid (KDO) is a prominent constituent of the cell-surface macromolecules of Gram-negative bacterial, and recently has also been found\* as a component of the cell walls of higher plants. In the bacterial lipopolysaccharides (US), KDO occurs as an cu-D-ketosidic component