Journal of Carbohydrate Chemistry p. 28 - 40 (2015)
Update date:2022-08-30
Topics:
Cao, Zhiling
Qu, Yingying
Zhou, Jiexing
Liu, Weiwei
Yao, Guowei
This article describes the stereoselective synthesis of quercetin 3-O-glycosides of 2-amino-2-deoxy-d-glucose. Efficient 1,2-trans-glycosylation of protected quercetin with N-acetyl-protected 2-amino-2-deoxy-d-glucose chloride was achieved under phase transfer catalytic conditions in a 0.15 M aqueous K2CO3/chloroform system using tetrabutylammonium bromide as the catalyst. On the contrary, glycosylation with the N-phthalimido-protected bromide donor under the same conditions was found to give predominantly 1,2-cis-glycoside product.
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