(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 | 927662-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 927662-10-0
• 化学式: C₅₃H₇₀O₉Si
• 分子量: 879.219
• InChiKey: XKULNKQOSMMSAL-AIHKBBDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.98
• 重原子数：
  63
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (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 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 水 为溶剂， 以56%的产率得到(1S,3R,5S,10R,12S,14R,16S,18R,19S,21R)-7,7-ditert-butyl-19,21-dimethyl-18-phenylmethoxy-19-(2-phenylmethoxyethyl)-2,6,8,11,15,20-hexaoxa-7-silapentacyclo[12.9.0.03,12.05,10.016,21]tricosane
  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 platinum(IV) oxide 三丁基膦 、 甲基锂 、 氢气 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 121.92h， 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,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

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.