(1S,2S,6E,10S,12R,13S,14R,17R,19R,20E,24R,26R)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-2-((2-nitrophenyl)selanyl)-9,27-dioxabicyclo[24.1.0]heptacosa-6,20-diene-8,15-dione | 1033588-22-5

• 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: (1S,2S,6E,10S,12R,13S,14R,17R,19R,20E,24R,26R)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-2-((2-nitrophenyl)selanyl)-9,27-dioxabicyclo[24.1.0]heptacosa-6,20-diene-8,15-dione
• CAS: 1033588-22-5
• 化学式: C₃₈H₅₅NO₁₀Se
• 分子量: 764.815
• InChiKey: UXIMMBXJUQZBJI-AGNIQOHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  50.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  179.96
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,6E,10S,12R,13S,14R,17R,19R,20E,24R,26R)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-2-((2-nitrophenyl)selanyl)-9,27-dioxabicyclo[24.1.0]heptacosa-6,20-diene-8,15-dione 在 双(三甲基硅基)过氧化物 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以65%的产率得到(1R,2E,6E,10S,12R,13S,14R,17R,19R,20E,24R,26R)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-9,27-dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione
  参考文献：
  名称：

  Total Synthesis of Cytotoxic Macrolide Amphidinolide B₁ and the Proposed Structure of Amphidinolide B₂

  摘要：

  The first enantioselective total syntheses of cytotoxic macrolide amphidinolide B, and the proposed structure for amphidinolide B-2 have been accomplished. Key features of the syntheses include a diastereoselective aldol condensation, a spontaneous Wadsworth-Emmons `macrocyclization and a directed epoxidation/elimination sequence.

  DOI：

  10.1021/ja803012n
• 作为产物：
  描述：

  2-硝基苯基丝氰酸酯 在 三丁基膦 、 三(二甲氨基)锍二氟三甲基硅酸 、 水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (1S,2S,6E,10S,12R,13S,14R,17R,19R,20E,24R,26R)-13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-2-((2-nitrophenyl)selanyl)-9,27-dioxabicyclo[24.1.0]heptacosa-6,20-diene-8,15-dione
  参考文献：
  名称：

  Amphidinolide B: Total Synthesis, Structural Investigation, and Biological Evaluation

  摘要：

  The total syntheses of amphidinolide B-1 and the proposed structure of amphidinolide B-2 have been accomplished. Key aspects of this work include the development of a practical, non-transitionmetal-mediated method for the construction of the C-13-C-15 diene, the identification of alpha-chelation and dipole minimization models for diastereoselective methyl ketone aldol reactions, the discovery of a spontaneous Horner-Wadsworth-Emmons macrocyclization strategy, and the development of a novel late stage method for construction of an allylic epoxide moiety. The originally proposed structure for amphidinolide B-2 and diastereomers thereof display potent antitumor activities with IC50 values ranging from 3.3 to 94.5 nM against human solid and blood tumor cells. Of the different stereoisomers, the proposed structure of amphidinolide B-2 is over 12-fold more potent than the C-8,C-9-epimer and C-18-epimer in human DU145 prostate cancer cells. These data suggest that the epoxide stereochemistry is a significant factor for anticancer activity.

  DOI：

  10.1021/jo3026077