Regioselective Glycodesilylation of Silylated Glycosides as a Useful Tool for the Preparation of Oligosaccharides
| Autor: | Elisabeth Eckhardt, Thomas Ziegler, G. Pantkowski |
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| Rok vydání: | 1994 |
| Předmět: | |
| Zdroj: | Journal of Carbohydrate Chemistry. 13:81-109 |
| ISSN: | 1532-2327 0732-8303 |
| DOI: | 10.1080/07328309408009180 |
| Popis: | A series of fully or partially protected alkyl and aryl 4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-d-glycopyranosides and 1-thio-β-d-glucopyranosides, respectively, were glycosylated by acetylated α-d-glucopyranosyl-, galactopyranosyl- and cellobiosyl fluoride under Lewis acid-catalysis to give the corresponding β-(1→6)-linked di- and trisaccharides, respectively, in moderate to high yield. With benzylated glucopyranosyl fluoride, anomeric mixtures of disaccharides were obtained depending on the solvent that was used for the glycosylation step. The initially formed oligosaccharides having a 1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl substituent at position 4 were converted by treatment with tetrabutylammonium fluoride into the corresponding 4-OH compounds which are suitable as glycosyl acceptors for further extension of the sugar chain. Selective glycodesilylation of methyl 2-O-benzoyl-6-O-dimethylthexylsilyl-3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-d-glucopyr... |
| Databáze: | OpenAIRE |
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