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trans ‐Stilbene C ‐Glycosides: Synthesis by a Microwave‐Assisted Heck Reaction and Evaluation of the SGLT‐2 Inhibitory Activity
Author(s) -
Kumar Ponnapalli Kalyana,
Kumar Adak Avijit,
Das Anindya,
Song JenShin,
Wu SzuHuei,
Sun ChungMing,
Lin ChunCheng
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700148
Subject(s) - chemistry , heck reaction , glycosyl , aryl , glycoside , selectivity , glycosyl donor , organic chemistry , coupling reaction , combinatorial chemistry , catalysis , stereochemistry , alkyl
A protocol for the microwave‐assisted Heck coupling reaction of C ‐aryl glycosides and styrenes has been developed for the synthesis of mono‐ and bis( C ‐glycoside) stilbenes. This method exclusively provides C ‐glycoside trans ‐stilbenes in good yields. The Pd‐catalyzed Heck coupling reaction was successfully applied to various functionalized C ‐glycosyl aryl iodides and various substituted styrenes to deliver several C ‐glycoside trans ‐stilbenes with high selectivity. The obtained C ‐glycosyl trans ‐stilbenes were also examined for human SGLT‐2 inhibitory activity.