Nabamita Basu, Sajal K Maity, Soumik Roy, Shuvendu Singha, Rina Ghosh
Department of Chemistry, Jadavpur University, Kolkata 700 032, India.
Carbohydrate research 2011 Apr 1Glycosides 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
PMID: 21333276
View Full Text