Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-[(4R,4aS,6R,8aR)-6-((1E,3E)-5-hydroxy-1,5-dimethyl-hexa-1,3-dienyl)-4,4a-dimethyl-decahydro-naphthalen-1-yloxy]-tetrahydro-pyran-3-yl ester | 133470-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-[(4R,4aS,6R,8aR)-6-((1E,3E)-5-hydroxy-1,5-dimethyl-hexa-1,3-dienyl)-4,4a-dimethyl-decahydro-naphthalen-1-yloxy]-tetrahydro-pyran-3-yl ester
• CAS: 133470-55-0
• 化学式: C₃₁H₄₈O₉
• 分子量: 564.717
• InChiKey: XEXCEKJNEMSLNJ-PVRMQKMYSA-N

反应信息

• 作为产物：
  描述：

  乙酸酐 、 fuscoside A 在 吡啶 作用下， 反应 3.0h， 以65%的产率得到Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-[(4R,4aS,6R,8aR)-6-((1E,3E)-5-hydroxy-1,5-dimethyl-hexa-1,3-dienyl)-4,4a-dimethyl-decahydro-naphthalen-1-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Fuscosides A-D: anti-inflammatory diterpenoid glycosides of new structural classes from the caribbean gorgonian Eunicea fusca

  摘要：

  Four new diterpenoid arabinose glycosides, fuscosides A-D (1,3,5, and 6), have been isolated from the Caribbean gorgonian Eunicea fusca Duchassaing and Michelotti. Fuscoside A (1) is a diterpenoid 2'-O-acetylarabinose glycoside possessing a new bicyclic carbon skeleton related in biosynthetic origin to the eremophilane class of sesquiterpenoids. The structures of these new compounds were assigned on the basis of chemical and spectral studies. Fuscosides A and B (1, 3) are effective topical antiinflammatory agents with potencies equivalent to indomethacin and manoalide. Fuscoside B (3) selectively inhibits the synthesis of leukotrienes LTB4 and LTC4, but not PGE2, in the mouse peritoneal macrophage, suggesting it is a selective inhibitor of leukotriene synthesis.

  DOI：

  10.1021/jo00009a042