(2E,6R)-6-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}hex-2-ene-1,6-diol | 881890-83-1

• 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: (2E,6R)-6-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}hex-2-ene-1,6-diol
• 英文别名: (E,6R)-6-[(2R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxan-2-yl]hex-2-ene-1,6-diol
• CAS: 881890-83-1
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: WVIAKYCKGWSMBG-LUGGRYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,6R)-6-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}hex-2-ene-1,6-diol 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 4 A molecular sieve 、 sodium hydride 、 (+)-Weinsaeure-diethylester 、 三乙胺 作用下， 以 甲醇 、 异辛烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2S,6R)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-{(2R,5R)-5-[(R)-oxiran2-yl]-tetrahydrofuran-2-yl}-tetrahydrofuran-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
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 2-[(2R,6S)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-yl]-2-hydroxy-ethyl ester 在 copper(l) iodide 、 四氧化锇 、 N-甲基吲哚酮 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 (2E,6R)-6-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}hex-2-ene-1,6-diol
  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

文献信息

• Molecular Simplification in Bioactive Molecules:  Formal Synthesis of (+)-Muconin
  作者：Fernando R. Pinacho Crisóstomo、Romen Carrillo、Leticia G. León、Tomás Martín、José M. Padrón、Víctor S. Martín

  DOI：10.1021/jo0524674

  日期：2006.3.1

  [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.