(4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide | 909270-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide
• 英文别名: (5R)-5-[(1R)-1-[tert-butyl(diphenyl)silyl]oxypentadecyl]oxolan-2-one
• CAS: 909270-41-3
• 化学式: C₃₅H₅₄O₃Si
• 分子量: 550.897
• InChiKey: UEDKYBVINHJLQW-CZNDPXEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide 在 diisobutyllithium hydride 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 127.0h， 生成 (2E,6R,7R)-7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2-henicosen-1-ol
  参考文献：
  名称：

  Convergent Synthesis of Pyragonicin

  摘要：

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.

  DOI：

  10.1021/jo060970q
• 作为产物：
  描述：

  heptadec-1-en-3-ol 在 2,6-二甲基吡啶 、 甲基磺酰胺 、 AD-mix-β 、 丙酸 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 96.5h， 生成 (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide
  参考文献：
  名称：

  Convergent Synthesis of Pyragonicin

  摘要：

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.

  DOI：

  10.1021/jo060970q

文献信息

• Convergent Synthesis of Pyragonicin
  作者：Shunya Takahashi、Yayoi Hongo、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/jo060970q

  日期：2006.8.1

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.