trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

Kalyana Kumar Ponnapalli, Avijit Kumar Adak, Anindya Das, Jen Shin Song, Szu Huei Wu, Chung-Ming Sun, Chun Cheng Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1308-1321
Number of pages14
JournalAsian Journal of Organic Chemistry
Volume6
Issue number9
DOIs
StatePublished - 1 Sep 2017

Keywords

  • cross-coupling
  • glycosylation
  • inhibitors
  • microwave chemistry
  • palladium

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