(1S,4S)-1-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-4-((2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl)butane-1,4-diol | 1186497-63-1

• 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: (1S,4S)-1-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-4-((2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl)butane-1,4-diol
• 英文别名: (1S,4S)-1-[(2S,5R)-5-hex-5-enyloxolan-2-yl]-4-[(2S,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butane-1,4-diol
• CAS: 1186497-63-1
• 化学式: C₂₉H₅₄O₅
• 分子量: 482.745
• InChiKey: SSOMUYDTGRBIOK-TVRBBCNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4S)-1-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-4-((2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl)butane-1,4-diol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(5S,8S)-5-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-8-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecane
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959
• 作为产物：
  描述：

  (R)-1-((2R,5S)-5-((5S,8S)-3,10-di-tert-butyl-8-((2S,5R)-5-((S)-1-(di-tert-butylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,11,11-tetramethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)hex-5-enyl methanesulfonate 在 六氟异丙醇 、 zinc diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以88%的产率得到(1S,4S)-1-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-4-((2S,5R)-5-((S)-1-hydroxyundecyl)tetrahydrofuran-2-yl)butane-1,4-diol
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959

文献信息

• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.