(αR,βR,2R,3S,4R)-3-bromo-α,2,4-trimethyl-β-trimethylsilyloxytetrahydrofuran-2-propanal | 286458-71-7

• 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: (αR,βR,2R,3S,4R)-3-bromo-α,2,4-trimethyl-β-trimethylsilyloxytetrahydrofuran-2-propanal
• 英文别名: (2R,3R)-3-[(2R,3S,4R)-3-bromo-2,4-dimethyloxolan-2-yl]-2-methyl-3-trimethylsilyloxypropanal
• CAS: 286458-71-7
• 化学式: C₁₃H₂₅BrO₃Si
• 分子量: 337.329
• InChiKey: YJKWXCGZVNKQCY-OFTGVCEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (αR,βR,2R,3S,4R)-3-bromo-α,2,4-trimethyl-β-trimethylsilyloxytetrahydrofuran-2-propanal 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 10.75h， 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：

  {(E)-(S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,4-dimethyl-pent-2-enyloxy}-tert-butyl-dimethyl-silane 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 N-溴代丁二酰亚胺(NBS) 、 amberlyst-15 resin 、 草酰氯 、 L-(+)-酒石酸二异丙酯 、 四丁基氟化铵 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 乙醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 40.58h， 生成 (αR,βR,2R,3S,4R)-3-bromo-α,2,4-trimethyl-β-trimethylsilyloxytetrahydrofuran-2-propanal
  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

• Anti Aldol Selectivity in a Synthetic Approach to the C₁−C₁₂ Fragment of the Tedanolides
  作者：Michael E. Jung、Ting-hu Zhang

  DOI：10.1021/ol702729u

  日期：2008.1.1

  In a synthetic approach to the completely protected C-1-C-12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.
• Synthesis of the C₁−C₁₂ Fragment of the Tedanolides. Aldol−Non-Aldol Aldol Approach
  作者：Michael E. Jung、Dongwon Yoo

  DOI：10.1021/ol0714038

  日期：2007.8.1

  The combination of highly stereoselective non-aldol aldol and aldol processes allows the preparation of the completely protected C-1-C-12 fragment 2 of the novel macrocyclic cytotoxic agent tedanolide 1.
• Synthesis of the C1–C12 fragment of the tedanolides. Selective hydroboration–protonation of allylic alcohol approach
  作者：Michael E. Jung、Dongwon Yoo

  DOI：10.1016/j.tetlet.2007.11.181

  日期：2008.1

  The combination of highly stereoselective vinyllithium addition and hydroboration-protonation of the resulting allylic alcohol permits the preparation of the completely protected C-1-C-12 fragment 2 of the novel macrocyclic cytotoxic agent tedanolide 1. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.