methyl 3-[(3S,3aS,11aS,11bR)-3-[tert-butyl(dimethyl)silyl]oxy-7,9-dihydroxy-3a-methyl-1,2,3,4,5,11b-hexahydrocyclopenta[c]xanthen-11a-yl]propanoate | 1276688-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 3-[(3S,3aS,11aS,11bR)-3-[tert-butyl(dimethyl)silyl]oxy-7,9-dihydroxy-3a-methyl-1,2,3,4,5,11b-hexahydrocyclopenta[c]xanthen-11a-yl]propanoate
• CAS: 1276688-55-1
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: IZHRMHOMUHPMCF-GXVHRJHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(3S,3aS,9bS)-7-methoxy-3a-methyl-1,2,3,4,5,6,9,9b-octahydrocyclopenta[a]naphthalen-3-yl]oxy-tert-butyl-dimethylsilane 在 盐酸 、 lead(IV) tetraacetate 、 zinc(II) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 水 、 苯 为溶剂， 反应 41.0h， 生成 methyl 3-[(3S,3aS,11aS,11bR)-3-[tert-butyl(dimethyl)silyl]oxy-7,9-dihydroxy-3a-methyl-1,2,3,4,5,11b-hexahydrocyclopenta[c]xanthen-11a-yl]propanoate 、
  参考文献：
  名称：

  Total Synthesis of Cortistatins A and J

  摘要：

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

  DOI：

  10.1021/jo2002616

文献信息

• Total Synthesis of Cortistatins A and J
  作者：Shuji Yamashita、Kentaro Iso、Kazuki Kitajima、Masafumi Himuro、Masahiro Hirama

  DOI：10.1021/jo2002616

  日期：2011.4.15

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.