(S)-1-(2R,5R)-5-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}(tetrahydrofuran-2-yl)ethene-1,2-diol | 881890-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(2R,5R)-5-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}(tetrahydrofuran-2-yl)ethene-1,2-diol
• 英文别名: (S)-1-((2R,5R)-5-((2R,6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-2H-pyran-2-yl)tetrahydrofuran-2-yl)ethane-1,2-diol；(1S)-1-[(2R,5R)-5-[(2R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxan-2-yl]oxolan-2-yl]ethane-1,2-diol
• CAS: 881890-91-1
• 化学式: C₁₆H₂₈O₆
• 分子量: 316.395
• InChiKey: ROCSSGXVGZJPEP-MZHQWRCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-(2R,5R)-5-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}(tetrahydrofuran-2-yl)ethene-1,2-diol 在 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 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：

  (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 、 (+)-Weinsaeure-diethylester 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到(S)-1-(2R,5R)-5-{(2R,6S)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}(tetrahydrofuran-2-yl)ethene-1,2-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

• A General Diastereoselective Strategy for Both <i>cis</i>- and <i>trans</i>-2,6-Disubstituted Tetrahydropyrans: Formal Total Synthesis of (+)-Muconin
  作者：Beduru Srinivas、D. Srinivas Reddy、N. Arjunreddy Mallampudi、Debendra K. Mohapatra

  DOI：10.1021/acs.orglett.8b03053

  日期：2018.11.2

  A protocol for general diastereoselective tandem dihydroxylation followed by SN2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. The application of this novel method was demonstrated through the concise formal synthesis of (+)-muconin, a nonclassical acetogenin, with sequential THP–THF

  提出了一种通用的非对映选择性串联二羟基化方法，然后将其S N 2环化，以从ζ-甲磺酰氧基α，β-不饱和酯方便有效地合成顺式和反式-2,6-二取代的四氢吡喃。这种新方法的应用通过非常规产乙酸素（+）-粘蛋白的简明形式合成以及依次形成THP-THF环得到了证明。
• 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.