(E)-methyl 2-((S)-6-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-((S)-1-(tert-butyldimethylsilyloxy)-4-(trimethylsilyl)but-3-ynyl)-2,3-dihydropyran-4-ylidene)acetate | 1027086-70-9

• 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: (E)-methyl 2-((S)-6-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-((S)-1-(tert-butyldimethylsilyloxy)-4-(trimethylsilyl)but-3-ynyl)-2,3-dihydropyran-4-ylidene)acetate
• 英文别名: methyl (2E)-2-[(2S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-4-trimethylsilylbut-3-ynyl]-6-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,3-dihydropyran-4-ylidene]acetate
• CAS: 1027086-70-9
• 化学式: C₃₂H₅₀O₆Si₂
• 分子量: 586.916
• InChiKey: HYFXQIUIJPAZSY-ZEYLVBMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-((S)-6-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-((S)-1-(tert-butyldimethylsilyloxy)-4-(trimethylsilyl)but-3-ynyl)-2,3-dihydropyran-4-ylidene)acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以96%的产率得到(E)-methyl 2-((S)-6-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-((S)-1-(tert-butyldimethylsilyloxy)but-3-ynyl)-2,3-dihydropyran-4-ylidene)acetate
  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：

  (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 在 双(乙腈)氯化钯(II) 、 三(2,6-二甲氧基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以60%的产率得到(E)-methyl 2-((S)-6-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-((S)-1-(tert-butyldimethylsilyloxy)-4-(trimethylsilyl)but-3-ynyl)-2,3-dihydropyran-4-ylidene)acetate
  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