Expeditious Synthesis of Tri- and Tetrahydroxyazepanes from d-(−)-Quinic Acid as Potent Glycosidase Inhibitors
學年 95
學期 2
出版（發表）日期 2007-05-25
作品名稱 Expeditious Synthesis of Tri- and Tetrahydroxyazepanes from d-(−)-Quinic Acid as Potent Glycosidase Inhibitors
作品名稱（其他語言）
著者 Shih, Tzenge-lien; Yang, Ru-ying; Li, Shiou-ting; Chiang, Cheng-fan; Lin, Chun-hung
單位 淡江大學化學學系
出版者 Washington: American Chemical Society
著錄名稱、卷期、頁數 Journal of Organic Chemistry 72(11), pp.4258-4261
摘要 Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an efficient manner. The key step employs dihydroxylation of protected chiral 1,4,5-cyclohex-2-enetriols under RuCl3/NaIO4/phosphate buffer (pH 7) condition, followed by reductive amino cyclization. We found the choice of an appropriate protecting group to C1-OH of chiral 1,4,5-cyclohex-2-enetriols would increase the yields of cyclization. The preliminary biological data indicate some of these azepanes possess potent inhibition against alpha-mannosidase and alpha-fucosidase.
關鍵字
語言 en
ISSN 1520-6904
期刊性質 國外
收錄於 SCI
產學合作
通訊作者 Shih, Tzenge-lien; Lin, Chun-hung
審稿制度 否
國別 USA
公開徵稿
出版型式 ,電子版,紙本
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