(4S,7R,8R,11R,12R)-8,12-oxido-4,7,11-tri(methoxymethoxy)-1-hexacosene | 860267-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,7R,8R,11R,12R)-8,12-oxido-4,7,11-tri(methoxymethoxy)-1-hexacosene
• 英文别名: (2R,3R,6R)-6-[(1R,4S)-1,4-bis(methoxymethoxy)hept-6-enyl]-3-(methoxymethoxy)-2-tetradecyloxane
• CAS: 860267-74-9
• 化学式: C₃₂H₆₂O₇
• 分子量: 558.84
• InChiKey: OXUSBONJTOVFGG-NYDDOVQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  39
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,7R,8R,11R,12R)-8,12-oxido-4,7,11-tri(methoxymethoxy)-1-hexacosene 在 Grubbs catalyst first generation 盐酸 、 sodium acetate 、 间氯过氧苯甲酸 、 对甲苯磺酰肼 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 pyragonicin
  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：

  (7R,8R,11R,12R)-8,12-oxido-7,11-di(methoxymethoxy)-1-hexacosen-4-ol 、 溴甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以97%的产率得到(4S,7R,8R,11R,12R)-8,12-oxido-4,7,11-tri(methoxymethoxy)-1-hexacosene
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126

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.
• Total Synthesis of the Proposed Structure for Pyragonicin
  作者：Shunya Takahashi、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/ol0508126

  日期：2005.6.1

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.