(2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(R)-oxiran-2-yl]-tetrahydro-2H-pyran | 881890-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(R)-oxiran-2-yl]-tetrahydro-2H-pyran
• 英文别名: (2S,6R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(2R)-oxiran-2-yl]oxane
• CAS: 881890-84-2
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: MXQKNEKGFDQJKT-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(R)-oxiran-2-yl]-tetrahydro-2H-pyran 在 copper(l) iodide 、 四氧化锇 、 N-甲基吲哚酮 、 二异丁基氢化铝 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 (2R,3S,7R,8R,11R,12R)-1,2-(isopropylidenedioxy)-3,7:8,11-dioxido-12-tetracosanol
  参考文献：
  名称：

  Molecular Simplification in Bioactive Molecules:  Formal Synthesis of (+)-Muconin

  摘要：

  [GRAPHICS]The concept of molecular simplification as a drug design strategy to shorten synthetic routes, while keeping or enhancing the biological activity of the lead drug, has been applied to (+)-muconin, an acetogenin with remarkable cytotoxicity. A novel approach that enables the stereoselective synthesis of such a natural compound or its enantiomer from a common precursor is described. An additional advantage of the method is complete stereochemical control and the decrease in the number of chemical steps required, thus providing an enhancement of the overall yield. Antiproliferative studies against the human solid tumor cell lines showed that the aliphatic chain-THF/THP fragment of (+)-muconin has modest cytotoxic activity. The strategy opens the way to preparing novel bioactive acetogenin analogues by shorter synthetic routes.

  DOI：

  10.1021/jo0524674
• 作为产物：
  描述：

  (2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethynyl-tetrahydro-2H-pyran 在 Lindlar's catalyst 吡啶 、 喹啉 、 AD-mix-α 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 (2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(R)-oxiran-2-yl]-tetrahydro-2H-pyran
  参考文献：
  名称：

  Molecular Simplification in Bioactive Molecules:  Formal Synthesis of (+)-Muconin

  摘要：

  [GRAPHICS]The concept of molecular simplification as a drug design strategy to shorten synthetic routes, while keeping or enhancing the biological activity of the lead drug, has been applied to (+)-muconin, an acetogenin with remarkable cytotoxicity. A novel approach that enables the stereoselective synthesis of such a natural compound or its enantiomer from a common precursor is described. An additional advantage of the method is complete stereochemical control and the decrease in the number of chemical steps required, thus providing an enhancement of the overall yield. Antiproliferative studies against the human solid tumor cell lines showed that the aliphatic chain-THF/THP fragment of (+)-muconin has modest cytotoxic activity. The strategy opens the way to preparing novel bioactive acetogenin analogues by shorter synthetic routes.

  DOI：

  10.1021/jo0524674