5-[(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]-4-[(2R,3S,5R,6S)-2-ethenyl-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-yl]oxypent-1-en-3-one | 927662-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(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]-4-[(2R,3S,5R,6S)-2-ethenyl-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-yl]oxypent-1-en-3-one
• CAS: 927662-05-3
• 化学式: C₅₅H₇₂O₉Si
• 分子量: 905.257
• InChiKey: TUWFNMQQVAFQAU-FLHOKFSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.56
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-[(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]-4-[(2R,3S,5R,6S)-2-ethenyl-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-yl]oxypent-1-en-3-one 在 ruthenium ethylidene complex 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 3.0h， 生成 (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-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 、 戴斯-马丁氧化剂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 32.92h， 生成 5-[(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]-4-[(2R,3S,5R,6S)-2-ethenyl-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-yl]oxypent-1-en-3-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

文献信息

• Convergent Synthesis of the CDEF Ring Fragment of Yessotoxin via a-Cyano Ethers
  作者：Tohru Oishi、Miho Suzuki、Koji Watanabe、Michio Murata

  DOI：10.3987/com-06-s(o)23

  日期：——

  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.