(5S,6S)-methyl 6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)nona-2,8-diynoate | 1027086-54-9

• 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: (5S,6S)-methyl 6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)nona-2,8-diynoate
• 英文别名: methyl (5S,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-9-trimethylsilylnona-2,8-diynoate
• CAS: 1027086-54-9
• 化学式: C₁₉H₃₄O₄Si₂
• 分子量: 382.648
• InChiKey: FFQAEZSPQHCGRW-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  (R)-1-methoxy-4-(((2-methylbut-3-yn-1-yl)oxy)methyl)benzene 、 (5S,6S)-methyl 6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)nona-2,8-diynoate 在 palladium diacetate 、 三(2,6-二甲氧基苯基)磷 作用下， 以 苯 为溶剂， 反应 10.5h， 以65%的产率得到(5S,6S,E)-methyl 3-((R)-4-(4-methoxybenzyloxy)-3-methylbut-1-ynyl)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)non-2-en-8-ynoate
  参考文献：
  名称：

  Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide

  摘要：

  A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.

  DOI：

  10.1021/ol800347u
• 作为产物：
  描述：

  (S)-2-((S)-1-(tert-butyldimethylsilyloxy)-4-(trimethylsilyl)but-3-ynyl)oxirane 、 丙炔酸甲酯 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 以85%的产率得到(5S,6S)-methyl 6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)nona-2,8-diynoate
  参考文献：
  名称：

  Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide

  摘要：

  A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.

  DOI：

  10.1021/ol800347u

文献信息

• Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide
  作者：Barry M. Trost、Brandon L. Ashfeld

  DOI：10.1021/ol800347u

  日期：2008.5.1

  A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.