tert-butyl-[(3S,8S,9S,10R,11S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-dimethylsilane | 871247-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: tert-butyl-[(3S,8S,9S,10R,11S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-dimethylsilane
• CAS: 871247-23-3
• 化学式: C₃₃H₆₀O₄Si₂
• 分子量: 577.008
• InChiKey: GNGZRIWHFKAGIR-OUJFNRDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.08
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3S,8S,9S,10R,11S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-dimethylsilane 在 2,6-二甲基吡啶 、 ammonium cerium (IV) nitrate 、 硼烷四氢呋喃络合物 、 叔丁基二甲硅基三氟甲磺酸酯 、 potassium tert-butylate 、 N-甲基吗啉氧化物 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.5h， 生成 1-((3S,5S,6S,8S,9S,10S,11S,13S,14S,17S)-3,6,11-tris((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
  参考文献：
  名称：

  海星皂角总皂苷B的全合成

  摘要：

  明星品质：人参皂甙B（一种来自海星人魔皂甙的反式除垢剂，具有防污活性）已经聚合了21个步骤，从肾上腺素开始的总收率为4.3％。这代表了复杂的星形皂苷的首次合成，该蛋白在海星中作为防御化学物质无处不在且具有特征性（见图）。

  DOI：

  10.1002/chem.201301186
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 17,17-ethylenedioxy-androst-5-ene-3β,11β-diol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以84%的产率得到tert-butyl-[(3S,8S,9S,10R,11S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-dimethylsilane
  参考文献：
  名称：

  The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187

  摘要：

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.

  DOI：

  10.1021/jo051556d

文献信息

• The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187
  作者：Zihao Hua、David A. Carcache、Yuan Tian、Yue-Ming Li、Samuel J. Danishefsky

  DOI：10.1021/jo051556d

  日期：2005.11.1

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.
• Total Synthesis of Starfish Saponin Goniopectenoside B
  作者：Guozhi Xiao、Biao Yu

  DOI：10.1002/chem.201301186

  日期：2013.6.10

  Star quality: Goniopectenoside B, a minor asterosaponin from starfish Goniopecten demonstrans with antifouling activity, has been synthesized in a convergent 21 steps and in 4.3 % overall yield starting from adrenosterone. This represents the first synthesis of a complex asterosaponin, which are ubiquitous and characteristic in starfish as defense chemicals (see figure).

  明星品质：人参皂甙B（一种来自海星人魔皂甙的反式除垢剂，具有防污活性）已经聚合了21个步骤，从肾上腺素开始的总收率为4.3％。这代表了复杂的星形皂苷的首次合成，该蛋白在海星中作为防御化学物质无处不在且具有特征性（见图）。