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| Titel: |
Lanthanum Trifluoromethane-sulfonate-Catalyzed Facile Synthesis of Per-O-acetylated Sugars and Their One-Pot Conversion to S-Aryl and O-Alkyl/Aryl Glycosides |
| Auteur: |
Dasgupta, Somnath Rajput, Vishal Kumar Roy, Bimalendu Mukhopadhyay, Balaram |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 26 (2007) nr. 2 pagina's 91-106 |
| Jaar: |
2007-03 |
| Inhoud: |
Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 2 van 5 gevonden artikelen
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