(8R,9R,12R,13R)-13-(tert-butyldimethylsilyloxy)-9,12-epoxy-pentacosa-1,6-diyn-8-ol | 685091-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (8R,9R,12R,13R)-13-(tert-butyldimethylsilyloxy)-9,12-epoxy-pentacosa-1,6-diyn-8-ol
• 英文别名: (1R)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolan-2-yl]octa-2,7-diyn-1-ol
• CAS: 685091-63-8
• 化学式: C₃₁H₅₆O₃Si
• 分子量: 504.869
• InChiKey: RJLGGTNSJXNCBS-SKKKGAJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9R,12R,13R)-13-(tert-butyldimethylsilyloxy)-9,12-epoxy-pentacosa-1,6-diyn-8-ol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium acetate 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 为溶剂， 反应 11.5h， 生成 (5S)-3-[(2R,13R)-2-(tert-butyldimethylsilyloxy)-13-hydroxy-13-[(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyloxy)tridecyl]tetrahydrofuran-2-yl]tridecyl]-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  murisolins的全合成和肿瘤生长抑制活性的评估。

  摘要：

  穆里索林（1），天然16,19-顺式-穆里斯林2和非天然16,19-顺式-穆里斯林3的聚合总合成是通过α-四氢呋喃醛与二炔和Sonogashira与γ-内酯的不对称烷基化反应完成的细分作为关键步骤。合成具有高光学纯度的α-四氢呋喃醛的立体异构体，并以高收率和高非对映选择性进行这些与1,6-庚二炔的不对称炔基化反应。还研究了合成化合物1-3的细胞生长抑制特征和COMPARE分析。

  DOI：

  10.1002/chem.200500462
• 作为产物：
  描述：

  1,6-庚二炔 、 (2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxytridecyl]oxolane-2-carbaldehyde 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 以84%的产率得到(8R,9R,12R,13R)-13-(tert-butyldimethylsilyloxy)-9,12-epoxy-pentacosa-1,6-diyn-8-ol
  参考文献：
  名称：

  murisolins的全合成和肿瘤生长抑制活性的评估。

  摘要：

  穆里索林（1），天然16,19-顺式-穆里斯林2和非天然16,19-顺式-穆里斯林3的聚合总合成是通过α-四氢呋喃醛与二炔和Sonogashira与γ-内酯的不对称烷基化反应完成的细分作为关键步骤。合成具有高光学纯度的α-四氢呋喃醛的立体异构体，并以高收率和高非对映选择性进行这些与1,6-庚二炔的不对称炔基化反应。还研究了合成化合物1-3的细胞生长抑制特征和COMPARE分析。

  DOI：

  10.1002/chem.200500462

文献信息

• First total synthesis of murisolinElectronic Supplementary Information (ESI) available: characterization data of synthetic murisolin (1), and 1H and 13C NMR spectra of compounds 9, 12 and 1. See http://www.rsc.org/suppdata/cc/b3/b312362f/
  作者：Naoyoshi Maezaki、Hiroaki Tominaga、Naoto Kojima、Minori Yanai、Daisuke Urabe、Tetsuaki Tanaka

  DOI：10.1039/b312362f

  日期：——

  The first and concise total synthesis of murisolin (1) was accomplished using asymmetric alkynylation and Sonogashira coupling as the key steps. The threo/trans/threo-type THF ring moiety was constructed with excellent stereoselectivity by asymmetric alkynylation of 1,6-heptadiyne to α-tetrahydrofuranic aldehyde, which was also prepared via the asymmetric alkynylation.

  以不对称炔化和 Sonogashira 偶联为关键步骤，首次简明地全合成了 murisolin (1)。1,6-庚二炔与α-四氢呋喃醛的不对称炔化反应，以优异的立体选择性构建了三/反/反式四氢呋喃环分子，α-四氢呋喃醛也是通过不对称炔化反应制备的。
• Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines
  作者：Naoto Kojima、Yuki Suga、Hiromi Hayashi、Takao Yamori、Takehiko Yoshimitsu、Tetsuaki Tanaka

  DOI：10.1016/j.bmcl.2011.08.011

  日期：2011.10

  The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated gamma-lactone fragment. It was revealed that the number of fluorine atoms on the gamma-lactone moiety affects the growth inhibitory activities against human cancer cell lines. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines
  作者：Naoto Kojima、Hiromi Hayashi、Satoshi Suzuki、Hiroaki Tominaga、Naoyoshi Maezaki、Tetsuaki Tanaka、Takao Yamori

  DOI：10.1016/j.bmcl.2008.10.069

  日期：2008.12

  C4-Fluorinated analogues of solamin, an antitumor acetogenin, were synthesized and investigated for their antitumor activities against 39 tumor cell lines. C4-Fluorinated solamins showed more potent growth inhibitory activity against cancer cell lines than solamin. (C) 2008 Elsevier Ltd. All rights reserved.
• Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I
  作者：Naoto Kojima、Masato Abe、Yuki Suga、Kazufumi Ohtsuki、Tetsuaki Tanaka、Hiroki Iwasaki、Masayuki Yamashita、Hideto Miyoshi

  DOI：10.1016/j.bmcl.2013.01.018

  日期：2013.3

  C34-epi and C34-epi-C35-trifluoro analogues of solamin, a mono-THF annonaceous acetogenin, were synthesized. Their inhibitory activity, along with previously synthesized analogues (C35-fluoro, C35-difluoro, and C35-trifluorosolamins), against bovine mitochondrial NADH-ubiquinone oxidoreductase (complex I) was determined. The present study revealed that the methyl group on the gamma-lactone moiety is critical to the potent inhibition of complex I by natural acetogenins. (c) 2013 Elsevier Ltd. All rights reserved.