4-(((2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2,6-dimethyl-2-vinyltetrahydro-2H-pyran-3-yl)oxy)-5-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)pent-1-en-3-ol | 927662-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(((2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2,6-dimethyl-2-vinyltetrahydro-2H-pyran-3-yl)oxy)-5-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)pent-1-en-3-ol
• CAS: 927662-04-2
• 化学式: C₅₅H₇₄O₉Si
• 分子量: 907.273
• InChiKey: IBEUDEMKFPFTOM-HGYNUHMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.35
• 重原子数：
  65.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(((2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2,6-dimethyl-2-vinyltetrahydro-2H-pyran-3-yl)oxy)-5-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)pent-1-en-3-ol 在 ruthenium ethylidene complex 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2S,3R,4aS,6S,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-dihydro-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)-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)-3-triethylsilyloxyoxan-2-yl]acetonitrile 在 三丁基膦 、 甲基锂 、 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 25.92h， 生成 4-(((2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2,6-dimethyl-2-vinyltetrahydro-2H-pyran-3-yl)oxy)-5-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-(naphthalen-2-ylmethoxy)hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)pent-1-en-3-ol
  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