(S)-3-((2R,5S)-5-Hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-butyric acid tert-butyl ester | 713122-79-3

• 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: (S)-3-((2R,5S)-5-Hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-butyric acid tert-butyl ester
• CAS: 713122-79-3
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: ZFKWKBWCQDQKRA-GVXVVHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((2R,5S)-5-Hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-butyric acid tert-butyl ester 在 Wilkinson's catalyst 、 氢气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到(S)-3-((2S,3R,5S)-5-Hydroxymethyl-3-methyl-tetrahydro-furan-2-yl)-butyric acid tert-butyl ester
  参考文献：
  名称：

  A Concise and Stereoselective Synthesis of the A-Ring Fragment of the Gambieric Acids

  摘要：

  The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.

  DOI：

  10.1021/ol049483s
• 作为产物：
  描述：

  (3S)-3-[(2R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-oxooxolan-2-yl]butanoic acid 在 草酰氯 、 四丁基氟化铵 、 四氯化钛 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (S)-3-((2R,5S)-5-Hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-butyric acid tert-butyl ester
  参考文献：
  名称：

  A Concise and Stereoselective Synthesis of the A-Ring Fragment of the Gambieric Acids

  摘要：

  The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.

  DOI：

  10.1021/ol049483s