(7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione | 172268-78-9

• 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,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione
• CAS: 172268-78-9
• 化学式: C₅₀H₇₈O₇Si₂
• 分子量: 847.336
• InChiKey: DYLFVCKMFPEFMV-AFVUMWMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.25
• 重原子数：
  59.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.05h， 以87%的产率得到(+)-5-(tert-butyldiphenylsilanyloxy)-acutiphycin
  参考文献：
  名称：

  Total Synthesis of (+)-Acutiphycin

  摘要：

  [GRAPHICS]Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel -catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SMI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.

  DOI：

  10.1021/jo701821h
• 作为产物：
  描述：

  (1R,5R,7E,9R,11R,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one 在 2,6-二甲基吡啶 、 戴斯-马丁氧化剂 作用下， 生成 (7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione
  参考文献：
  名称：

  Total Syntheses of (+)-Acutiphycin and (+)-trans-20,21-Didehydroacutiphycin

  摘要：

  DOI：

  10.1021/ja00153a031

文献信息

• Total Syntheses of (+)-Acutiphycin and (+)-<i>trans</i>-20,21-Didehydroacutiphycin
  作者：Amos B. Smith、Sean S.-Y. Chen、Frances C. Nelson、Janice M. Reichert、Brian A. Salvatore

  DOI：10.1021/ja972497r

  日期：1997.11.1

  The first total syntheses of the cytotoxic macrolides (+)-acutiphycin (1) and (+)-trans-20,21-didehydroacutiphycin (2) have been achieved. An acyclic stereocontrol strategy was employed to establish the configurations at C(5), C(10), and C(13) as well as the E geometry of the C(8,9)-trisubstituted olefin. Importantly, the natural source of 1 and 2, the blue-green alga Osillatoria acutissima, no longer produces these metabolites.