(4R,5R,7R)-methyl 4,5-bis(diisopropyl-(3,3,4,4,4-penta-fluoro-butyl)-silyloxy)-7-(triisopropylsilyloxy)deca-2,9-dienoate | 1374332-42-9

• 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: (4R,5R,7R)-methyl 4,5-bis(diisopropyl-(3,3,4,4,4-penta-fluoro-butyl)-silyloxy)-7-(triisopropylsilyloxy)deca-2,9-dienoate
• 英文别名: methyl (2E,4R,5R,7R)-4,5-bis[[3,3,4,4,4-pentafluorobutyl-di(propan-2-yl)silyl]oxy]-7-tri(propan-2-yl)silyloxydeca-2,9-dienoate
• CAS: 1374332-42-9
• 化学式: C₄₀H₇₂F₁₀O₅Si₃
• 分子量: 907.249
• InChiKey: BPMJQBQHEXMBKN-MVRWKZEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.72
• 重原子数：
  58
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4S,5S,7R,2E)-methyl 4,5,7-tris(triisopropylsilyloxy)deca-2,9-dienoate 、 (4S,5S,7S,)-methyl 7-(diisopropyl(3,3,4,4,4-pentafluorobutyl)silyloxy)-4,5-bis(triisopropylsilyloxy)deca-2,9-dienoate 、 (4R,5R,7R)-methyl 4,5-bis(diisopropyl-(3,3,4,4,4-penta-fluoro-butyl)-silyloxy)-7-(triisopropylsilyloxy)deca-2,9-dienoate 、 (4R,5R,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,5S,7R,E)-4,5,7-tris(triisopropylsilyloxy)deca-2,9-dienoic acid 、 、 (4R,5R,7R,E)-4,5-bis((diisopropyl(3,3,4,4,4-pentafluorobutyl)silyl)oxy)-7-((triisopropylsilyl)oxy)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：

  (2E,4E)-methyl 7-((4-methoxybenzyl)oxy)hepta-2,4-dienoate 在 2,6-二甲基吡啶 、 甲基磺酰胺 、 三氟甲磺酸 、 AD-mix β 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 36.58h， 生成 (4R,5R,7R)-methyl 4,5-bis(diisopropyl-(3,3,4,4,4-penta-fluoro-butyl)-silyloxy)-7-(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