tert-butyl N-[(1S,2R,5S,6S,14S,16R)-5-[tert-butyl(dimethyl)silyl]oxy-6-methyl-12-oxo-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-14-yl]carbamate | 1276688-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl N-[(1S,2R,5S,6S,14S,16R)-5-[tert-butyl(dimethyl)silyl]oxy-6-methyl-12-oxo-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-14-yl]carbamate
• CAS: 1276688-65-3
• 化学式: C₃₀H₄₇NO₅Si
• 分子量: 529.792
• InChiKey: JUFBCFOGEYXZQK-FYXZZENXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2R,5S,6S,14S,16R)-14-azido-5-[tert-butyl(dimethyl)silyl]oxy-6-methyl-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-12-one 在 lithium aluminium tetrahydride 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.0h， 生成 tert-butyl N-[(1S,2R,5S,6S,14S,16R)-5-[tert-butyl(dimethyl)silyl]oxy-6-methyl-12-oxo-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-14-yl]carbamate
  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.