[3,10,11,12-2H]-(3S,5Z,8Z)-3-tert-butyldiphenylsilyloxytetradeca-5,8-dienoic acid propyl ester | 421546-82-9

• 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: [3,10,11,12-2H]-(3S,5Z,8Z)-3-tert-butyldiphenylsilyloxytetradeca-5,8-dienoic acid propyl ester
• 英文别名: propyl (3S,5Z,8Z)-3-[tert-butyl(diphenyl)silyl]oxy-3,10,11,12-tetradeuteriotetradeca-5,8-dienoate
• CAS: 421546-82-9
• 化学式: C₃₃H₄₈O₃Si
• 分子量: 524.796
• InChiKey: QIHZJAOMBUNZCR-VARREUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3,10,11,12-2H]-(3S,5Z,8Z)-3-tert-butyldiphenylsilyloxytetradeca-5,8-dienoic acid propyl ester 在 氢氧化钾 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 水 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：

  1,3-丙酮二羧酸 在 镍 咪唑 、 盐酸 、 sodiym bis-silyl amide 、 硼烷 、 三乙胺 、 氘 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 丙醇 、 phosphate buffer 、 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 [3,10,11,12-2H]-(3S,5Z,8Z)-3-tert-butyldiphenylsilyloxytetradeca-5,8-dienoic 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

文献信息

• Biosynthetic Precursors of the Lipase Inhibitor Lipstatin
  作者：Christoph A. Schuhr、Wolfgang Eisenreich、Markus Goese、Peter Stohler、Wolfgang Weber、Ernst Kupfer、Adelbert Bacher

  DOI：10.1021/jo016285v

  日期：2002.4.1

  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.