gigantetrocin A | 160399-32-6

• 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: gigantetrocin A
• 英文别名: (2S)-4-[(2R)-2-hydroxy-7-[(2R,5S)-5-[(1S,4R,5R)-1,4,5-trihydroxynonadecyl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
• CAS: 160399-32-6
• 化学式: C₃₅H₆₄O₇
• 分子量: 596.889
• InChiKey: VFRBLIGIRLWBKM-JBSVHPCSSA-N

物化性质

• 沸点：
  760.2±50.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  42
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二甲基亚砜 、 gigantetrocin A 在 三甲基氯硅烷 作用下， 生成 Gigantetrocin A 17,18-formaldehyde acetal 、 Gigantetrocin A 14,17-formaldehyde acetal
  参考文献：
  名称：

  Determining Absolute Configurations of Stereocenters in Annonaceous Acetogenins through Formaldehyde Acetal Derivatives and Mosher Ester Methodology

  摘要：

  Formaldehyde (methylene) acetal derivatives can be conveniently prepared, on a small scale, using parent Annonaceous acetogenins which have 1,2-, 1,4-, and/or 1,5-diols along their aliphatic chains. The resulting cyclic acetal protons give NMR signals which allow characterization of the relative stereochemistries of the two stereogenic centers that originated from the diols. Less complicated (vs the parent acetogenins) per-Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] derivatives of the acetal derivatives can then be prepared and used to determine absolute configurations of the chiral positions which bear the remaining free hydroxyls. Prior knowledge of relative stereochemical relationships then permits assignments of absolute configurations to additional chiral centers along the chain of the molecules. This method has been particularly useful in solving the absolute configurations of several nonadjacent bis-THF and mono-THF acetogenins, viz. bullatanocin (1), (2,4-cis and trans)-bullatanocinones (2 and 3), bullatalicin (4), (2,4-cis and trans)-bullatalicinones (5 and 6), squamostatin A (7), squamocin (8), gigantetrocin A (9), and goniothalamicin (10). Most of the resulting acetals (vs the parent acetogenins) show enhanced, bioactivities, and their mode of action is, likewise, by mitochondrial inhibition.

  DOI：

  10.1021/jo00097a017
• 作为产物：
  描述：

  (5S,6S)-5,6-dihydroxydeca-1,9-diene 在 palladium on activated charcoal 叔丁基过氧化氢 、 sodium periodate 、 Wilkinson's catalyst 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 potassium dioxotetrahydroxoosmate(VI) 、 2,3-二巯基丁二酸 、 Co(modp)2 、 三氟化硼乙醚 、 potassium tert-butylate 、 氢气 、 氧气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 异丙醇 、 叔丁醇 、 苯 为溶剂， 生成 gigantetrocin A
  参考文献：
  名称：

  A facile route to the total synthesis of gigantetrocin A

  摘要：

  A highly efficient synthetic method of the trans-mono-tetrahydrofuran (THF) ring building block was established and the title compound synthesized in 19 steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00039-7

文献信息

• Absolute Stereochemistries of Giganin and Longanin, Bioactive Non-tetrahydrofuran Ring Annonaceous Acetogenins from Asimina longifolia
  作者：Jerry L. McLaughlin、Qing Ye、Dean Evert

  DOI：10.3987/com-96-7515

  日期：——
• A facile route to the total synthesis of gigantetrocin A
  作者：Zhi-Min Wang、Shi-Kai Tian、Min Shi

  DOI：10.1016/s0957-4166(99)00039-7

  日期：1999.2

  A highly efficient synthetic method of the trans-mono-tetrahydrofuran (THF) ring building block was established and the title compound synthesized in 19 steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Determining Absolute Configurations of Stereocenters in Annonaceous Acetogenins through Formaldehyde Acetal Derivatives and Mosher Ester Methodology
  作者：Z. Gu、Lu Zeng、X. Fang、Trina Colman-Saizarbitoria、Mei Huo、Jerry L. McLaughlin

  DOI：10.1021/jo00097a017

  日期：1994.9

  Formaldehyde (methylene) acetal derivatives can be conveniently prepared, on a small scale, using parent Annonaceous acetogenins which have 1,2-, 1,4-, and/or 1,5-diols along their aliphatic chains. The resulting cyclic acetal protons give NMR signals which allow characterization of the relative stereochemistries of the two stereogenic centers that originated from the diols. Less complicated (vs the parent acetogenins) per-Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] derivatives of the acetal derivatives can then be prepared and used to determine absolute configurations of the chiral positions which bear the remaining free hydroxyls. Prior knowledge of relative stereochemical relationships then permits assignments of absolute configurations to additional chiral centers along the chain of the molecules. This method has been particularly useful in solving the absolute configurations of several nonadjacent bis-THF and mono-THF acetogenins, viz. bullatanocin (1), (2,4-cis and trans)-bullatanocinones (2 and 3), bullatalicin (4), (2,4-cis and trans)-bullatalicinones (5 and 6), squamostatin A (7), squamocin (8), gigantetrocin A (9), and goniothalamicin (10). Most of the resulting acetals (vs the parent acetogenins) show enhanced, bioactivities, and their mode of action is, likewise, by mitochondrial inhibition.