期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 44, 页码 14836-14851出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302572
关键词
anomerisation; glycuronic acid; Lewis acids; protecting groups; regioselectivity
资金
- Science Foundation Ireland [12/IA/1398]
- Roche Ireland, Ltd.
- Science Foundation Ireland (SFI) [12/IA/1398] Funding Source: Science Foundation Ireland (SFI)
Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5 equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75%) and stereoselectivies (alpha/beta> 9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the alpha 1 -> 4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful.
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