(7E,9E,11E,13E,15E)-(1S,3S,5R,19S,20S,23S,25S,27S,29R,31R,33S,35R)-3,23,25,27,29,31,35-Heptahydroxy-19-isopropyl-16,20-dimethyl-18,37,38-trioxa-tricyclo[31.3.1.1^1,5]octatriaconta-7,9,11,13,15-pentaen-17-one | 157089-05-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (7E,9E,11E,13E,15E)-(1S,3S,5R,19S,20S,23S,25S,27S,29R,31R,33S,35R)-3,23,25,27,29,31,35-Heptahydroxy-19-isopropyl-16,20-dimethyl-18,37,38-trioxa-tricyclo[31.3.1.1^1,5]octatriaconta-7,9,11,13,15-pentaen-17-one
• CAS: 157089-05-9
• 化学式: C₄₀H₆₄O₁₁
• 分子量: 720.942
• InChiKey: UXURUFVELWKJSC-JQOILYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  51.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  186.37
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (7E,9E,11E,13E,15E)-(1S,3S,5R,19S,20S,23S,25S,27S,29R,31R,33S,35R)-3,23,25,27,29,31,35-Heptahydroxy-19-isopropyl-16,20-dimethyl-18,37,38-trioxa-tricyclo[31.3.1.1^1,5]octatriaconta-7,9,11,13,15-pentaen-17-one 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以58.4 mg的产率得到(7E,9E,11E,13E,15E)-(1S,3S,5R,19S,20S,23S,25S,27S,29S,31S,33S,35R)-3,23,25,27,29,31,35-Heptakis-(tert-butyl-dimethyl-silanyloxy)-19-isopropyl-16,20-dimethyl-18,37,38-trioxa-tricyclo[31.3.1.1^1,5]octatriaconta-7,9,11,13,15-pentaen-17-one
  参考文献：
  名称：

  Stereochemical Determination of Roflamycoin: 13C Acetonide Analysis and Synthetic Correlation

  摘要：

  The relative configuration of natural roflamycoin (1) was determined by C-13 acetonide analysis, combined with other supporting spectroscopic data. A previous proposal for the configuration of roflamycoin was shown to be incorrect. The absolute configuration was determined by the advanced Mosher's method. Our proposed structure of natural roflamycoin was confirmed by the synthesis of a degradation fragment that incorporates all of the 11 independent stereogenic centers of roflamycoin. The complete structure of roflamycoin is illustrated in Figure 1.

  DOI：

  10.1021/ja00106a024
• 作为产物：
  描述：

  roflamycoin 在 Dowex 50W-X₁ acid resin 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以58 mg的产率得到(7E,9E,11E,13E,15E)-(1S,3S,5R,19S,20S,23S,25S,27S,29R,31R,33S,35R)-3,23,25,27,29,31,35-Heptahydroxy-19-isopropyl-16,20-dimethyl-18,37,38-trioxa-tricyclo[31.3.1.1^1,5]octatriaconta-7,9,11,13,15-pentaen-17-one
  参考文献：
  名称：

  Stereochemical Determination of Roflamycoin: 13C Acetonide Analysis and Synthetic Correlation

  摘要：

  The relative configuration of natural roflamycoin (1) was determined by C-13 acetonide analysis, combined with other supporting spectroscopic data. A previous proposal for the configuration of roflamycoin was shown to be incorrect. The absolute configuration was determined by the advanced Mosher's method. Our proposed structure of natural roflamycoin was confirmed by the synthesis of a degradation fragment that incorporates all of the 11 independent stereogenic centers of roflamycoin. The complete structure of roflamycoin is illustrated in Figure 1.

  DOI：

  10.1021/ja00106a024