| 201465-90-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 201465-90-9
• 化学式: C₂₉H₃₉BrO₆
• 分子量: 563.529
• InChiKey: SPEHYNPNDMBLHU-SJWCDYLKSA-N

物化性质

• 沸点：
  630.698±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.371±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  36.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 Nafion H 、 二丁基二氯化锡 、 tetramethylguanidinum azide 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Interphylal Product Splicing:  The First Total Syntheses of Cephalostatin 1, the North Hemisphere of Ritterazine G, and the Highly Active Hybrid Analogue, Ritterostatin G_N1_N¹

  摘要：

  Convergent total syntheses of the extremely potent cell growth inhibitor cephalostatin 1 and two hybrid analogues, ritterostatins G(N)1(N) and G(N)1(S), have been achieved. Ritterostatin G(N)1(N) displays sub-nanomolar activity in the 60 cell line human tumor panel of the National Cancer Institute. The North hemisphere of ritterazine G was efficiently constructed from hecogenin acetate in 15% yield over 13 steps. Extension of a key photolysis/Prins sequence to intermediates 19 and 32 proceeded in excellent yield, leading to installation of the Delta(14) moiety in the-North G-and South I steroidal subunits. Application of a method for directed unsymmetrical coupling furnished the natural and analogue pyrazines in good yield from the cephalostatin and ritterazine components.

  DOI：

  10.1021/ja972160p
• 作为产物：
  描述：

  (1R,2S,3'R,5R,6S,7S,10S,11R,13S,14S,17S,19S)-17-[tert-butyl(diphenyl)silyl]oxy-5',5',6,14-tetramethyl-3'-phenylmethoxyspiro[8-oxapentacyclo[11.8.0.02,10.05,10.014,19]henicosane-7,2'-oxolane]-11-ol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 jones reagent 、 PTAB 、 TEA 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 铬酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 40.85h， 生成
  参考文献：
  名称：

  Interphylal Product Splicing:  The First Total Syntheses of Cephalostatin 1, the North Hemisphere of Ritterazine G, and the Highly Active Hybrid Analogue, Ritterostatin G_N1_N¹

  摘要：

  Convergent total syntheses of the extremely potent cell growth inhibitor cephalostatin 1 and two hybrid analogues, ritterostatins G(N)1(N) and G(N)1(S), have been achieved. Ritterostatin G(N)1(N) displays sub-nanomolar activity in the 60 cell line human tumor panel of the National Cancer Institute. The North hemisphere of ritterazine G was efficiently constructed from hecogenin acetate in 15% yield over 13 steps. Extension of a key photolysis/Prins sequence to intermediates 19 and 32 proceeded in excellent yield, leading to installation of the Delta(14) moiety in the-North G-and South I steroidal subunits. Application of a method for directed unsymmetrical coupling furnished the natural and analogue pyrazines in good yield from the cephalostatin and ritterazine components.

  DOI：

  10.1021/ja972160p

文献信息

• A Practical Synthesis of Cephalostatin 1
  作者：Yong Shi、Lanqi Jia、Qing Xiao、Quan Lan、Xiaohu Tang、Dahai Wang、Min Li、Yu Ji、Tao Zhou、Weisheng Tian

  DOI：10.1002/asia.201000882

  日期：2011.3.1

  Let′s get practical: A new practical synthetic strategy for natural sterols starting from pregnan‐(16S,20S)‐diols and steroid‐(16S),22‐lactones is presented. A tandem double oxymercuration–demercuration and a substitution–ketalization cascade are considered as the key reactions for the construction of the spiroketal rings.

  让我们付诸实践：从pregnan-（16 S，20 S）-二醇和类固醇（16 S），22-内酯开始，提出一种新的天然甾醇实用合成策略。串联双氧汞化-脱汞和取代-缩酮化级联被认为是构建螺环的关键反应。