(2E,6R,7R)-methyl 7-t-(butyldiphenylsilyloxy)-6-hydroxy-2-henicosenate | 909270-42-4

• 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: (2E,6R,7R)-methyl 7-t-(butyldiphenylsilyloxy)-6-hydroxy-2-henicosenate
• 英文别名: methyl (E,6R,7R)-7-[tert-butyl(diphenyl)silyl]oxy-6-hydroxyhenicos-2-enoate
• CAS: 909270-42-4
• 化学式: C₃₈H₆₀O₄Si
• 分子量: 608.977
• InChiKey: NYQYPEXVNUPMAM-GUKDSWLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (2E,6R,7R)-methyl 7-t-(butyldiphenylsilyloxy)-6-hydroxy-2-henicosenate 在 titanium(IV) isopropylate 吡啶 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 diisobutyllithium hydride 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 苯甲酰氯 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 异辛烷 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 277.0h， 生成 (2R,3R,6R,7R)-6-methoxymethyloxy-1,2:3,7-diepoxy-henicosane
  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 、 二异丁基氢化铝 、 丙酸 作用下， 以 正己烷 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 102.5h， 生成 (2E,6R,7R)-methyl 7-t-(butyldiphenylsilyloxy)-6-hydroxy-2-henicosenate
  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.