[(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-[(3R)-3-methyl-4-(4-methylphenyl)sulfonyloxybutyl]-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate | 241465-95-2

• 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: [(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-[(3R)-3-methyl-4-(4-methylphenyl)sulfonyloxybutyl]-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate
• CAS: 241465-95-2
• 化学式: C₃₆H₅₀O₇S
• 分子量: 626.855
• InChiKey: XSDPBSQYPZVJID-HFQZEFIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-[(3R)-3-methyl-4-(4-methylphenyl)sulfonyloxybutyl]-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate 在 sodium iodide 作用下， 以99%的产率得到[(1R,2S,4S,8R,9S,12S,13S,16S,18S)-6-[(3R)-4-iodo-3-methylbutyl]-7,9,13-trimethyl-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate
  参考文献：
  名称：

  螺环的同时开环和卤化

  摘要：

  在中性条件下，用三苯基膦二卤化物将各种螺环化合物开环生成ω-卤代烯醇醚，收率好至极好。该方法甚至在低于先前报道的这种异构化开环的温度下也能转化非常稳定的乙酸血红素乙酸酯。

  DOI：

  10.1016/s0040-4039(99)00827-8
• 作为产物：
  描述：

  龙舌兰皂苷乙酯 在 4-甲基苯磺酸吡啶 、 potassium hydrogencarbonate 作用下， 生成 [(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-[(3R)-3-methyl-4-(4-methylphenyl)sulfonyloxybutyl]-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate
  参考文献：
  名称：

  螺环的同时开环和卤化

  摘要：

  在中性条件下，用三苯基膦二卤化物将各种螺环化合物开环生成ω-卤代烯醇醚，收率好至极好。该方法甚至在低于先前报道的这种异构化开环的温度下也能转化非常稳定的乙酸血红素乙酸酯。

  DOI：

  10.1016/s0040-4039(99)00827-8

文献信息

• 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
  作者：Thomas G. LaCour、Chuangxing Guo、Sudhakar Bhandaru、Michael R. Boyd、P. L. Fuchs

  DOI：10.1021/ja972160p

  日期：1998.2.1

  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.