(4S,6S)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(E,4S)-4-methyl-5-triethylsilyloxypent-2-en-2-yl]oxan-2-one | 172268-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,6S)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(E,4S)-4-methyl-5-triethylsilyloxypent-2-en-2-yl]oxan-2-one
• CAS: 172268-41-6
• 化学式: C₃₃H₅₀O₄Si₂
• 分子量: 566.929
• InChiKey: CKTPIAMTACIAKG-AOBVBSJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,6S)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(E,4S)-4-methyl-5-triethylsilyloxypent-2-en-2-yl]oxan-2-one 在 柠檬酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/ja972497r
• 作为产物：
  描述：

  (2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-tetrahydro-pyran-2-ol 在 silica gel 、 silver carbonate 作用下， 以93%的产率得到(4S,6S)-4-[tert-butyl(diphenyl)silyl]oxy-6-[(E,4S)-4-methyl-5-triethylsilyloxypent-2-en-2-yl]oxan-2-one
  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 (+)-trans-20,21-Didehydroacutiphycin
  作者：Amos B. Smith、Sean S.-Y. Chen、Frances C. Nelson、Janice M. Reichert、Brian A. Salvatore

  DOI：10.1021/ja00153a031

  日期：1995.12
• 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.