Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-¦Â-valienamine (NOEV) and N-octyl-¦Â-valienamine (NOV)

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• 作者：Shinichi  ; Kuno^a ;   ; ^{kuno-s@hokkochem.co.jp} ; Atsushi  ; Takahashi^a ; Seiichiro  ; Ogawa^b
• 关键词：Carbasugar ; Quercitol ; Valienamine ; Carbohydrate mimics ; Glycosidase inhibitors ; Structure&ndash ; activity relationship ; Chemical chaperone
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2011
• 出版时间：1 December 2011
• 年：2011
• 卷：21
• 期：23
• 页码：7189-7192
• 全文大小：271 K

文摘

(+)-proto-Quercitol (1) and (?-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-¦Â-valienamine (NOEV, 3) and N-octyl-¦Â-valienamine (NOV, 4).