(2R,3R,6R,7R)-6-methoxymethyloxy-1,2:3,7-diepoxy-henicosane | 860267-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,6R,7R)-6-methoxymethyloxy-1,2:3,7-diepoxy-henicosane
• 英文别名: (2R,3R,6R,7R)-1,2:3,7-dioxido-6-methoxymethoxy-heneicosane；(2R,3R,6R)-3-(methoxymethoxy)-6-[(2R)-oxiran-2-yl]-2-tetradecyloxane
• CAS: 860267-69-2
• 化学式: C₂₃H₄₄O₄
• 分子量: 384.6
• InChiKey: AXJDPGPDQXFIOE-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R,7R)-6-methoxymethyloxy-1,2:3,7-diepoxy-henicosane 在 四氧化锇 sodium periodate 、 copper(l) iodide 、 (-)-B-methoxydiisopinocamphenylborane 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 水 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 12.75h， 生成 (4S,7R,8R,11R,12R)-8,12-oxido-7,11-di(methoxymethoxy)-1-hexacosen-4-ol
  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
• 作为产物：
  描述：

  heptadec-1-en-3-ol 在 titanium(IV) isopropylate 吡啶 、 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 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 二异丁基氢化铝 、 苯甲酰氯 、 丙酸 、 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 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 379.5h， 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

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.