(2R,3S,7R,8R,11R,12R)-1,2-(isopropylidenedioxy)-3,7:8,11-dioxido-12-tetracosanol | 485322-65-4

• 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: (2R,3S,7R,8R,11R,12R)-1,2-(isopropylidenedioxy)-3,7:8,11-dioxido-12-tetracosanol
• 英文别名: (1R)-1-((2R,5R)-5-{(2R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}-tetrahydro-2-furanyl)-1-tridecanol；(1R)-1-[(2R,5R)-5-[(2R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxan-2-yl]oxolan-2-yl]tridecan-1-ol
• CAS: 485322-65-4
• 化学式: C₂₇H₅₀O₅
• 分子量: 454.691
• InChiKey: HIGHRWKSJGCHND-JMLBKQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,7R,8R,11R,12R)-1,2-(isopropylidenedioxy)-3,7:8,11-dioxido-12-tetracosanol 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟化硼乙醚 、 potassium carbonate 、 苯甲酰氯 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (S)-3-((E)-(2R,10S)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-10-{(2S,6R)-6-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tetrahydro-pyran-2-yl}-dec-5-en-7-ynyl)-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  全合成粘蛋白

  摘要：

  通过THF-THP链段与末端丁烯内酯的偶联反应合成了抗肿瘤产乙酸原素粘蛋白。关键反应包括环氧四醇的6- exo环化，羟基甲苯磺酸酯的区域选择性环化以及与Zn（BH 4）2相邻的2,6-顺式THP环的无环酮的立体选择性还原。

  DOI：

  10.1016/s0040-4039(02)02182-2
• 作为产物：
  描述：

  ethyl (2E,6R)-6-[(2R,6S)-6-{(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-tetrahydro-2H-pyran-2-yl}-6-hydroxy-2-hexenoate 在 二异丁基氢化铝 、 magnesium 作用下， 以 甲苯 为溶剂， 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

文献信息

• Total synthesis of muconin
  作者：Shunya Takahashi、Akemi Kubota、Tadashi Nakata

  DOI：10.1016/s0040-4039(02)02182-2

  日期：2002.11

  An antitumor acetogenin, muconin, was synthesized through a coupling reaction of a THF–THP segment and a terminal butenolide. The key reactions include 6-exo cyclization of an epoxy tetraol, regioselective cyclization of hydroxy tosylate, and stereoselective reduction of an acyclic ketone adjacent to the 2,6-cis THP ring with Zn(BH4)2.

  通过THF-THP链段与末端丁烯内酯的偶联反应合成了抗肿瘤产乙酸原素粘蛋白。关键反应包括环氧四醇的6- exo环化，羟基甲苯磺酸酯的区域选择性环化以及与Zn（BH 4）2相邻的2,6-顺式THP环的无环酮的立体选择性还原。
• 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.
• Stereoselective total synthesis of muconin
  作者：Shunya Takahashi、Akemi Kubota、Tadashi Nakata

  DOI：10.1016/s0040-4020(03)00135-2

  日期：2003.3

  muconin, was synthesized through a coupling reaction of a THF–THP segment and a terminal butenolide. The key reactions include successive ether-ring formation reaction under acidic and basic conditions or one-pot double cyclization promoted by TBAF and stereoselective reduction of acyclic ketones adjacent to the 2,6-cis THP with Zn(BH4)2.

  通过THF-THP链段与末端丁烯内酯的偶联反应合成了抗肿瘤产乙酸原素粘蛋白。关键反应包括在酸性和碱性条件下连续的醚环形成反应或由TBAF促进的一锅双环化和与Zn（BH 4）2相邻的2,6-顺式THP的无环酮的立体选择性还原。