An Efficient One-Pot Synthesis of Diastereomerically Pure 1,4-Dideoxy-1,4-Imino-D-Arabinitol from a chiral aziridine

Title
An Efficient One-Pot Synthesis of Diastereomerically Pure 1,4-Dideoxy-1,4-Imino-D-Arabinitol from a chiral aziridine
Authors
박동식최환근이원구심태보
Issue Date
2009-10
Publisher
대한화학회 학술대회
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/36329
Appears in Collections:
KIST Publication > Conference Paper
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