(2R,3S,5R,6S)-2-(2-hydroxyethyl)-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-ol | 927661-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,5R,6S)-2-(2-hydroxyethyl)-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-3-ol
• CAS: 927661-99-2
• 化学式: C₂₅H₃₄O₅
• 分子量: 414.542
• InChiKey: VVTDUURKCWMVMP-LIONHTAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 、 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 、 苯 为溶剂， 反应 29.42h， 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
• 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 二异丁基氢化铝 、 sodium tetrahydroborate 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 乙醇 、 四氢呋喃 为溶剂， 反应 2.5h， 以78%的产率得到(2R,3S,5R,6S)-2-(2-hydroxyethyl)-2,6-dimethyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-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

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.