(4S,5R,7S,2E)-methyl 7-(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate | 1374332-58-7

• 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: (4S,5R,7S,2E)-methyl 7-(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate
• 英文别名: methyl (2E,4S,5R,7S)-7-[3,3,4,4,4-pentafluorobutyl-di(propan-2-yl)silyl]oxy-4,5-bis[tri(propan-2-yl)silyloxy]deca-2,9-dienoate
• CAS: 1374332-58-7
• 化学式: C₃₉H₇₅F₅O₅Si₃
• 分子量: 803.27
• InChiKey: UQIKROYSXCKCPX-GRIKOJGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.54
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4S,5R,7R,)-methyl 4,5,7-tris(triisopropylsilyloxy)deca-2,9-dienoate 、 (4S,5R,7S,2E)-methyl 7-(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate 、 (4R,5S,7R)-methyl 4,5-bis(diisopropyl(3,3,4,4,4-pentafluorobutyl)silyloxy)-7-(triisopropylsilyloxy)deca-2,9-dienoate 、 (4R,5S,7S,E)-methyl 4,5,7-tris(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)deca-2,9-dienoate 、 potassium trimethylsilonate 以 乙醚 为溶剂， 反应 16.25h， 生成 (4S,5R,7R,E)-4,5,7-tris(triisopropylsilyloxy)deca-2,9-dienoic acid 、 、 、
  参考文献：
  名称：

  Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones

  摘要：

  Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.

  DOI：

  10.1021/ja302260d
• 作为产物：
  描述：

  (4S,5R,E)-methyl 4,5-bis(triisopropylsilyloxy)octa-2,7-dienoate 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 (-)-B-chlorodiisopinocampheylborane 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (4S,5R,7S,2E)-methyl 7-(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate 、 (4S,5R,7R,2E)-methyl-7-(diisopropyl-(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate
  参考文献：
  名称：

  Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones

  摘要：

  Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.

  DOI：

  10.1021/ja302260d