An Efficient One-Pot Synthesis of Diastereomerically Pure 1,4-Dideoxy-1,4-Imino-D-Arabinitol from a chiral aziridine
- An Efficient One-Pot Synthesis of Diastereomerically Pure 1,4-Dideoxy-1,4-Imino-D-Arabinitol from a chiral aziridine
- 박동식; 최환근; 이원구; 심태보
- Issue Date
- 대한화학회 학술대회
- 1,4-Dideoxy-1,4-imino-D-arabinitol first isolated from the fruits of Angylocalyx boutiqueanus in 1985 turned out to possesses a-glucosidase inhibitory activity. The a-glucosidase inhibitors have proved to block carbohydrate metabolism and been successfully launched on the drug market for diabetes treatment. Moreover, it has also been reported a-glucosidase inhibitors exhibit antitumor, antiviral and apoptosis-inducing activities. The broad spectrum of biological activity of a-glucosidase inhibitors led us to be interested in synthesizing 1,4-dideoxy-1,4-imino-D-arabinitol, a a-glucosidase inhibitor in highly efficient and stereoselective fashion. We would like to present a chiral aziridine could be readily transformed into 1,4-dideoxy-1,4-imino-D-arabinitol in one-pot and chirospecific manner via ring opening of chiral aziridine, followed by ring formation of five-membered imino sugar.
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