(2S,3R,4aS,6S,9aR)-3-(benzyloxy)-2-(2-(benzyloxy)ethyl)-6-(((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methyl)-2,9a-dimethylhexahydro-2H-pyrano[3,2-b]oxepin-7(6H)-one | 927662-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4aS,6S,9aR)-3-(benzyloxy)-2-(2-(benzyloxy)ethyl)-6-(((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methyl)-2,9a-dimethylhexahydro-2H-pyrano[3,2-b]oxepin-7(6H)-one
• CAS: 927662-09-7
• 化学式: C₅₃H₇₀O₉Si
• 分子量: 879.219
• InChiKey: XKULNKQOSMMSAL-VRGAMSDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.98
• 重原子数：
  63.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4aS,6S,9aR)-3-(benzyloxy)-2-(2-(benzyloxy)ethyl)-6-(((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methyl)-2,9a-dimethylhexahydro-2H-pyrano[3,2-b]oxepin-7(6H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 92.0h， 以84%的产率得到(2S,3R,4aS,6R,9aR)-6-[[(4aR,6S,7R,8aS)-2,2-ditert-butyl-7-(naphthalen-2-ylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]methyl]-2,9a-dimethyl-3-phenylmethoxy-2-(2-phenylmethoxyethyl)-4,4a,8,9-tetrahydro-3H-pyrano[3,2-b]oxepin-7-one
  参考文献：
  名称：

  Convergent Synthesis of the CDEF Ring Fragment of Yessotoxin via a-Cyano Ethers

  摘要：

  The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)(3) to afford the alpha-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

  DOI：

  10.3987/com-06-s(o)23
• 作为产物：
  描述：

  2-(((2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2,6-dimethyl-2-vinyltetrahydro-2H-pyran-3-yl)oxy)-3-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)propanal 在 platinum(IV) oxide 甲基锂 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.0h， 生成 (2S,3R,4aS,6S,9aR)-3-(benzyloxy)-2-(2-(benzyloxy)ethyl)-6-(((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methyl)-2,9a-dimethylhexahydro-2H-pyrano[3,2-b]oxepin-7(6H)-one
  参考文献：
  名称：

  Convergent Synthesis of the CDEF Ring Fragment of Yessotoxin via a-Cyano Ethers

  摘要：

  The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)(3) to afford the alpha-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

  DOI：

  10.3987/com-06-s(o)23