[3-2H]-(3S)-5-oxo-3-tert-butyldiphenylsilyloxypentanoic acid propyl ester | 420838-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: [3-2H]-(3S)-5-oxo-3-tert-butyldiphenylsilyloxypentanoic acid propyl ester
• 英文别名: propyl (3S)-3-[tert-butyl(diphenyl)silyl]oxy-3-deuterio-5-oxopentanoate
• CAS: 420838-45-5
• 化学式: C₂₄H₃₂O₄Si
• 分子量: 413.593
• InChiKey: IMLDAGNMBRGHGJ-HIDRZSPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-2H]-(3S)-5-oxo-3-tert-butyldiphenylsilyloxypentanoic acid propyl ester 在 氢氧化钾 、 sodiym bis-silyl amide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 [3,10,11,12-2H]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid
  参考文献：
  名称：

  Biosynthetic Precursors of the Lipase Inhibitor Lipstatin

  摘要：

  Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy. [3,10,11,12-H-2]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-H-2(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [C-13-formyl,N-15]-N-formylleucine (10) was diverted to lipstatin under loss of the C-13-labeled formyl residue.

  DOI：

  10.1021/jo016285v
• 作为产物：
  描述：

  [3-2H]-3-hydroxyglutaric acid dipropyl ester 在 咪唑 、 硼烷 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 phosphate buffer 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 [3-2H]-(3S)-5-oxo-3-tert-butyldiphenylsilyloxypentanoic acid propyl ester
  参考文献：
  名称：

  Biosynthetic Precursors of the Lipase Inhibitor Lipstatin

  摘要：

  Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy. [3,10,11,12-H-2]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-H-2(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [C-13-formyl,N-15]-N-formylleucine (10) was diverted to lipstatin under loss of the C-13-labeled formyl residue.

  DOI：

  10.1021/jo016285v