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Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl(3)-catalyzed (20 mol%) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl(3) also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4',6'-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn. Copyright © 2011 Elsevier Ltd. All rights reserved.


Nabamita Basu, Sajal K Maity, Soumik Roy, Shuvendu Singha, Rina Ghosh. FeCl3 mediated arylidenation of carbohydrates. Carbohydrate research. 2011 Apr 1;346(5):534-9

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PMID: 21333276

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