(3S,4S,7R,9R)-7,9-dihydroxy-3,4-(isopropylidenedioxy)-5-decenoic acid | 245107-90-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4S,7R,9R)-7,9-dihydroxy-3,4-(isopropylidenedioxy)-5-decenoic acid
• CAS: 245107-90-8
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: NDJCQDOABNCHTC-HGWXFACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,7R,9R)-7,9-dihydroxy-3,4-(isopropylidenedioxy)-5-decenoic acid 在 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以38%的产率得到Sodium; (E)-(3S,4S,7R,9R)-3,4,7,9-tetrahydroxy-dec-5-enoate
  参考文献：
  名称：

  Synthesis and biological testings as inhibitors of HMGCoA reductase of the seco-acid of tuckolide and its C-7 epimer

  摘要：

  The seco-acid of the natural macrolactone, tuckolide (decarestrictin D) and the C-7 epimer have been prepared in enantiomerically pure form from D-gluconolactone and poly(3-hydroxy butyric acid). The key steps are Horner-Emmons olefination and stereoselective reduction of the resulting enone to provide both epimers at C-7. None of the seco-acids inhibit microsomal HMGCoA reductase of pea or rat liver. It may be concluded that the cholesterol biosynthesis inhibiting effect of tuckolide is unlikely to proceed via HMGCoA reductase inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00020-6
• 作为产物：
  描述：

  (4R,5S)-methyl 5-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 lithium hydroxide 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium periodate 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 四丁基氟化铵 、 水 、 异丙基氯化镁 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 16.25h， 生成 (3S,4S,7R,9R)-7,9-dihydroxy-3,4-(isopropylidenedioxy)-5-decenoic acid
  参考文献：
  名称：

  Synthesis and biological testings as inhibitors of HMGCoA reductase of the seco-acid of tuckolide and its C-7 epimer

  摘要：

  The seco-acid of the natural macrolactone, tuckolide (decarestrictin D) and the C-7 epimer have been prepared in enantiomerically pure form from D-gluconolactone and poly(3-hydroxy butyric acid). The key steps are Horner-Emmons olefination and stereoselective reduction of the resulting enone to provide both epimers at C-7. None of the seco-acids inhibit microsomal HMGCoA reductase of pea or rat liver. It may be concluded that the cholesterol biosynthesis inhibiting effect of tuckolide is unlikely to proceed via HMGCoA reductase inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00020-6