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 | 927662-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 927662-03-1
• 化学式: C₅₃H₇₀O₉Si
• 分子量: 879.219
• InChiKey: JZJHGLNIRURXPL-WQQKWYHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.0
• 重原子数：
  63.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  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
• 作为产物：
  描述：

  (2R,3S,5R,6S)-2-(2-hydroxyethyl)-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-ol 在 三丁基膦 、 二异丁基氢化铝 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.42h， 生成 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
  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