期刊
CARBOHYDRATE RESEARCH
卷 346, 期 5, 页码 534-539出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2011.01.003
关键词
FeCl3; Benzylidenation; Arylidenation; Lewis acid; Catalyzed
资金
- CSIR, New Delhi, India
- FIST-DST, India [01/2382/10/EMR-II]
Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-0-arylidenation producing the corresponding acetals in high yields. FeCl3 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. (C) 2011 Elsevier Ltd. All rights reserved.
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