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제106회 대한화학회 학술발표회, 총회 및 기기전시회 안내 An Efficient synthesis of 5-membered iminosugars and (−)-Swainsonine from Chiral Aziridines

등록일
2010년 9월 1일 14시 12분 48초
접수번호
1602
발표코드
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발표시간
금 11시 : 30분
발표형식
구두발표
발표분야
유기화학 - 대학원생 구두발표
저자 및
공동저자
최환근, 심태보1, 이원구
서강대학교 화학과, Korea
1한국과학기술연구원 생체과학연구본부, Korea

1,4-dideoxy-1,4-imino-D-arabinitol and (−)-swainsonine were turned out to be a potent glycogen phophorylase inhibitor. The glucosidase inhibitors have aroused much interest on account of the possibility that these could be therapeutic agents for treating several diseases such as diabetes, viral infection, cancer and genetic disorder. The oncogene activation triggered the aberrant glycosylation due to an altered cascade expression of glycosyltransferases. It was also turned out that the level of glycosidases was elevated in many cancer patients. The broad spectrum of biological activity, especially anti-cancer activity, of α-glucosidase inhibitors led us to be interested in synthesizing stereoselectively 1,4-dideoxy-1,4-imino-D-arabinitol including its analogues and (−)-Swainsonine. An efficient and facial synthetic approach for the synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and its analogues was successfully achieved starting from commercially available chiral aziridines. In addition, an efficient synthesis of enantiomerically pure (−)-swainsonine was successfully accomplished using intramolecular cyclization of the amino alcohol which was derived from a readily available 1-(R)-α-methylbenzylaziridine-2-carboxylic acid (−)-menthol ester.


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