methyl (E,5R,7R)-7-[tert-butyl(diphenyl)silyl]oxy-5-hydroxyoct-2-enoate | 1286241-91-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E,5R,7R)-7-[tert-butyl(diphenyl)silyl]oxy-5-hydroxyoct-2-enoate
• CAS: 1286241-91-5
• 化学式: C₂₅H₃₄O₄Si
• 分子量: 426.628
• InChiKey: JELRHQURJOJMFD-CMOGAMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E,5R,7R)-7-[tert-butyl(diphenyl)silyl]oxy-5-hydroxyoct-2-enoate 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 三甲基铝 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 methyl (R,E)-4-((2S,4S,6R)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)propyl)-2-phenyl-1,3-dioxan-4-yl)pent-2-enoate
  参考文献：
  名称：

  Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

  摘要：

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].

  DOI：

  10.3987/com-10-12106
• 作为产物：
  描述：

  (2E,5R)-5-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hex-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲酸 、 L-(+)-酒石酸二乙酯 、 戴斯-马丁氧化剂 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (E,5R,7R)-7-[tert-butyl(diphenyl)silyl]oxy-5-hydroxyoct-2-enoate
  参考文献：
  名称：

  Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

  摘要：

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].

  DOI：

  10.3987/com-10-12106

文献信息

• Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions
  作者：Shinji Nagumo、Masaaki Miyashita、Hisashi Takada、Eiko Yasui、Megumi Mizukami

  DOI：10.3987/com-10-12106

  日期：——

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].