Efficient one-pot per-O-acetylation–thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation–acetylation of S-/O-glycosides catalyzed by Mg(OTf)2
| Autor: | Rina Ghosh, Aritra Chaudhury, Mana Mohan Mukherjee, Nabamita Basu |
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| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry General Chemical Engineering Disaccharide Glycoside Regioselectivity General Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis Benzaldehyde Dimethyl acetal chemistry.chemical_compound Acetylation Yield (chemistry) Organic chemistry |
| Zdroj: | RSC Advances. 6:109301-109314 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c6ra23198e |
| Popis: | A sequential one-pot per-O-acetylation–S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation–acetylation of mono and disaccharide based glycosides and thioglycosides in high yield. |
| Databáze: | OpenAIRE |
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