(2S,4S,5S,8S,10R)-10-O-(tert-butyldimethylsilyl)-8-hydroxy-1,2:4,5-di-(isopropylidenedioxy)-6-undecene | 245107-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S,8S,10R)-10-O-(tert-butyldimethylsilyl)-8-hydroxy-1,2:4,5-di-(isopropylidenedioxy)-6-undecene
• CAS: 245107-81-7
• 化学式: C₂₃H₄₄O₆Si
• 分子量: 444.684
• InChiKey: LLCFZYVALYRIJE-NXOMALCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S,8S,10R)-10-O-(tert-butyldimethylsilyl)-8-hydroxy-1,2:4,5-di-(isopropylidenedioxy)-6-undecene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以98%的产率得到(2S,4S,5S,8S,10R)-8,10-dihydroxy-1,2:4,5-di-(isopropylidenedioxy)-6-undecene
  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)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(imidazole-1-carbothioyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 在 lithium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 偶氮二异丁腈 、 异丙基氯化镁 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 16.5h， 生成 (2S,4S,5S,8S,10R)-10-O-(tert-butyldimethylsilyl)-8-hydroxy-1,2:4,5-di-(isopropylidenedioxy)-6-undecene
  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