(S)-2-[(2R,5S)-5-((S)-2-Hydroxy-pentyl)-tetrahydro-furan-2-yl]-propionic acid tert-butyl ester | 275356-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (S)-2-[(2R,5S)-5-((S)-2-Hydroxy-pentyl)-tetrahydro-furan-2-yl]-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(2R,5S)-5-[(2S)-2-hydroxypentyl]oxolan-2-yl]propanoate
• CAS: 275356-56-4
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: XPVJSACGIOFPAE-XDQVBPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (S)-2-[(2R,5S)-5-((S)-2-Hydroxy-pentyl)-tetrahydro-furan-2-yl]-propionic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2S,3R,6S,8S)-2-Methyl-3,6-epoxyundecane-1,8-diol
  参考文献：
  名称：

  Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group

  摘要：

  A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the tetrahydrofuran ring, was the chelation controlled E-Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration. (C) 2000 Elsevier Science Ltd. Air rights reserved.

  DOI：

  10.1016/s0040-4039(00)00251-3
• 作为产物：
  描述：

  2-[(S)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester 在 rhodium on alumina 四丁基氟化铵 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， -78.0 ℃ 、400.0 kPa 条件下， 反应 0.75h， 生成 (S)-2-[(2R,5S)-5-((S)-2-Hydroxy-pentyl)-tetrahydro-furan-2-yl]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group

  摘要：

  A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the tetrahydrofuran ring, was the chelation controlled E-Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration. (C) 2000 Elsevier Science Ltd. Air rights reserved.

  DOI：

  10.1016/s0040-4039(00)00251-3

文献信息

• A Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin-607, Pamamycin-593, and Pamamycin-621D Precursors
  作者：Steve Lanners、Hassan Norouzi-Arasi、Xavier J. Salom-Roig、Gilles Hanquet

  DOI：10.1002/anie.200701749

  日期：2007.9.17