[(1R,2S,4S,6S,7S,8R,9S,12S,13S,16S,18S)-5',5',7,9,13-pentamethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxolane]-16-yl] acetate | 201465-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2S,4S,6S,7S,8R,9S,12S,13S,16S,18S)-5',5',7,9,13-pentamethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxolane]-16-yl] acetate
• CAS: 201465-73-8
• 化学式: C₂₉H₄₄O₅
• 分子量: 472.665
• InChiKey: QWLZNHORBHRWLF-PPYRUDDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2S,4S,6S,7S,8R,9S,12S,13S,16S,18S)-5',5',7,9,13-pentamethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxolane]-16-yl] acetate 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 (2S,4aS,5S,6R,8aS)-4a-methyl-5-(2-oxoethyl)-6-((2S,3S,3aR,6aS)-3,4,5',5'-tetramethyl-3,3a,4',5',6,6a-hexahydro-3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5-yl)decahydronaphthalen-2-yl acetate
  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：

  龙舌兰皂苷乙酯 在 4-甲基苯磺酸吡啶 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 生成 [(1R,2S,4S,6S,7S,8R,9S,12S,13S,16S,18S)-5',5',7,9,13-pentamethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxolane]-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

• Ruthenium-Catalyzed Mild C−H Oxyfunctionalization of Cyclic Steroidal Ethers¹
  作者：Jong Seok Lee、Hui Cao、Philip L. Fuchs

  DOI：10.1021/jo070382s

  日期：2007.7.1

  Ruthenium-catalyzed site-specific C−H oxyfunctionalization of steroidal ethers with periodate or bromate as terminal oxidants in phosphate buffer provided the acid-sensitive C-16 hydroxy compounds in high yields. Phosphate buffer (pH 7.5) significantly inhibits formation of unwanted side products generated under more acidic reaction conditions. A key example is demonstrated at the 100 g scale.

  钌在磷酸盐缓冲液中以高碘酸盐或溴酸盐为末端氧化剂对甾族醚的钌催化位点特异性C-H羟基官能化提供了高收率的酸敏感性C-16羟基化合物。磷酸盐缓冲液（pH 7.5）可以显着抑制在更酸性的反应条件下生成的有害副产物的形成。以100克规模展示了一个关键的例子。