(2S)-4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-2-methyl-2H-furan-5-one | 1011298-70-6

• 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: (2S)-4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-2-methyl-2H-furan-5-one
• CAS: 1011298-70-6
• 化学式: C₂₂H₄₀O₃Si
• 分子量: 380.643
• InChiKey: AVBBFHDJRAFHDJ-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-2-methyl-2H-furan-5-one 、 (1R)-1-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-yl]but-3-en-1-ol 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以66%的产率得到
  参考文献：
  名称：

  Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity

  摘要：

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.

  DOI：

  10.1021/jm801028c
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 2.0h， 以410 mg的产率得到(2S)-4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions

  摘要：

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.089

文献信息

• Total Synthesis and Structure Confirmation of (−)-Asimitrin, a C₃₇ Annonaceous Acetogenin with a Hydroxylated Adjacent Bis-Tetrahydrofuran Core
  作者：Soo Yeon Kwak、Youngjik Park、Seongju Lim、Hongjun Jang、Dongjoo Lee、Hyoungsu Kim、Deukjoon Kim

  DOI：10.1021/acs.orglett.3c02495

  日期：2023.9.15

  The total synthesis and structure confirmation of the potent cytotoxic agent (−)-asimitrin (1), a C37 annonaceous acetogenin having a hydroxylated adjacent bis-tetrahydrofuran (THF) core, are described. The present synthesis features a highly stereoselective, chelate-controlled intramolecular amide enolate alkylation (IAEA) for the synthesis of key intermediate 17-hydroxy-16,17-erythro-16,19-trans-THF

  描述了强效细胞毒性剂(-)-阿西米特林( 1 )的全合成和结构确认，该药物是一种具有羟基化相邻双四氢呋喃(THF)核心的C 37番荔枝苷元。本合成采用高度立体选择性、螯合物控制的分子内酰胺烯醇烷基化 (IAEA)，用于合成关键中间体 17-羟基-16,17-赤式-16,19-反式-THF 6，我们的直接酮合成/ l -用于立体选择性引入 C(21)–C(34) 单元、Sharpless 不对称二羟基化 (SAD) 和内部 Williamson 醚化以构建 20,23-反式-THF 环的 Selectride 还原方案。
• Alteration of the Bis-tetrahydrofuran Core Stereochemistries in Asimicin Can Affect the Cytotoxicity
  作者：Subhash C. Sinha、Zhiyong Chen、Zheng-Zheng Huang、Eiko Nakamaru-Ogiso、Halina Pietraszkiewicz、Matthew Edelstein、Frederick Valeriote

  DOI：10.1021/jm801028c

  日期：2008.11.27

  A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.
• Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tet.2007.11.089

  日期：2008.2

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.