(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 | 180784-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 180784-82-1
• 化学式: C₁₇H₂₄N₂O₇S
• 分子量: 400.453
• InChiKey: AVQBTIAYTPPYEB-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  90.27
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以65%的产率得到(4R,5S)-methyl 5-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
  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：

  2,2-二甲氧基丙烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 (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
  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