(2S,3S,6R,7R)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol | 909270-37-7

• 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: (2S,3S,6R,7R)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol
• 英文别名: (3R,4R)-1-[(2S,3S)-3-(hydroxymethyl)oxiran-2-yl]-3-(methoxymethoxy)octadecan-4-ol
• CAS: 909270-37-7
• 化学式: C₂₃H₄₆O₅
• 分子量: 402.615
• InChiKey: USWOJSJGBQMTKD-LUKWVAJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,6R,7R)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到(2S,3R,6R,7R)-6-methoxymethyloxy-3,7-epoxy-henicosane-1,2-diol
  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 titanium(IV) isopropylate 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 甲基磺酰胺 、 4 A molecular sieve 、 AD-mix-β 、 diisobutyllithium hydride 、 四丁基氟化铵 、 二异丁基氢化铝 、 丙酸 、 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 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 339.5h， 生成 (2S,3S,6R,7R)-6-methoxymethyloxy-2,3-epoxy-henicosan-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

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.