(1S,2R,5S,6S,12S,14R,16R)-5-[tert-butyl(dimethyl)silyl]oxy-14-(dimethylamino)-6-methyl-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-12-ol | 1276688-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2R,5S,6S,12S,14R,16R)-5-[tert-butyl(dimethyl)silyl]oxy-14-(dimethylamino)-6-methyl-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-12-ol
• CAS: 1276688-63-1
• 化学式: C₂₇H₄₅NO₃Si
• 分子量: 459.745
• InChiKey: CQQAUEFXXFBLMY-SMAHHUDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,6S,12S,14R,16R)-5-[tert-butyl(dimethyl)silyl]oxy-14-(dimethylamino)-6-methyl-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-12-ol 在 甲基磺酰氯 、 N,N-二异丙基乙胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.28h， 以39%的产率得到(3S,3aS,9S,10aR,12aS,12bR)-3-((tert-Butyldimethylsilyl)oxy)-N,N,3a-trimethyl-1,2,3,3a,4,9,10,11,12,12b-decahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-9-amine
  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
• 作为产物：
  描述：

  (3S,3aS,10aS,12aS,12bR)-3-(tert-butyldimethylsiloxy)-3a-methyl-1,2,3,3a,4,9,10,11,12,12b-decahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]-inden-7(8H)-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 47.0h， 生成 (1S,2R,5S,6S,12S,14R,16R)-5-[tert-butyl(dimethyl)silyl]oxy-14-(dimethylamino)-6-methyl-19-oxapentacyclo[14.2.1.01,9.02,6.011,16]nonadeca-8,10-dien-12-ol
  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