(2R,3S,4R)-3-bromo-2-{(2R,3S)-3-[((1,1-dimethyl)ethyl)dimethylsilyloxy]methyl-3-methyloxiran-2-yl}-2,4-dimethyltetrahydrofuran | 286458-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,3S,4R)-3-bromo-2-{(2R,3S)-3-[((1,1-dimethyl)ethyl)dimethylsilyloxy]methyl-3-methyloxiran-2-yl}-2,4-dimethyltetrahydrofuran
• 英文别名: [(2S,3R)-3-[(2R,3S,4R)-3-bromo-2,4-dimethyloxolan-2-yl]-2-methyloxiran-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 286458-70-6
• 化学式: C₁₆H₃₁BrO₃Si
• 分子量: 379.41
• InChiKey: OXAITJQLFGMDHX-WALBABNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3-bromo-2-{(2R,3S)-3-[((1,1-dimethyl)ethyl)dimethylsilyloxy]methyl-3-methyloxiran-2-yl}-2,4-dimethyltetrahydrofuran 在 咪唑 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.75h， 生成 (αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-1-[(1S,2'S,3'S)-3-[[((1,1-dimethyl)ethyl)dimethylsilyloxy]methyl-3-methyloxiran-2-yl]ethyl]tetrahydrofuran-2-methanol methanesulfonate
  参考文献：
  名称：

  Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis

  摘要：

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

  DOI：

  10.1021/ol005675l
• 作为产物：
  描述：

  (2R,3S,4R)-3-bromo-2,4-dimethyl-2-((E)-2-methyl-3-hydroxy-1-propenyl)tetrahydrofuran 在 咪唑 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2R,3S,4R)-3-bromo-2-{(2R,3S)-3-[((1,1-dimethyl)ethyl)dimethylsilyloxy]methyl-3-methyloxiran-2-yl}-2,4-dimethyltetrahydrofuran
  参考文献：
  名称：

  Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis

  摘要：

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

  DOI：

  10.1021/ol005675l

文献信息

• Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis
  作者：Michael E. Jung、Rodolfo Marquez

  DOI：10.1021/ol005675l

  日期：2000.6.1

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.