期刊
CARBOHYDRATE RESEARCH
卷 344, 期 11, 页码 1340-1346出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2009.05.016
关键词
Resveratrol; Hydroxytyrosol; Urolithin-B; Glucuronic metabolites; Glycosylation reactions; Trichloroacetimidate donor
资金
- JAE-Doc program
- CSIC [200680F0132]
A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
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