[(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate | 481711-06-2

• 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-(3-methylbut-3-enyl)-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate
• CAS: 481711-06-2
• 化学式: C₂₉H₄₂O₄
• 分子量: 454.65
• InChiKey: LXQRSTDCYVFRRT-PUCXMBLBSA-N

物化性质

• 沸点：
  542.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

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-(3-methylbut-3-enyl)-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-16-yl] acetate 在 4-二甲氨基吡啶 、 TEA 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 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：

  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 吡啶 、 氢氧化钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 甲醇 为溶剂， 生成 [(1R,2S,4S,8R,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-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：

  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

• Chemospecific Chromium[VI] Catalyzed Oxidation of C−H Bonds at −40 °C
  作者：Seongmin Lee、P. L. Fuchs

  DOI：10.1021/ja026734o

  日期：2002.11.1

  H5IO6 in the presence of catalytic chromoyl diacetate is a powerful method for oxidation of C-H bonds. Tertiary and oxygen activated C-H bonds are oxidized to tertiary alcohols or ketones at temperatures as low as -40 degrees C. The putative reagent is neutral dioxoperoxy chromium[VI] which undergoes C-H oxidation with retention of stereochemistry. This reagent appears to be the first reagent capable of oxidation of a C-H bond in the presence of an olefin without concomitant epoxidation.