(αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-[(2S)-(E)-5-hydroxymethyl-4-methyl-3-penten-2-yl]tetrahydrofuran-2-methanol methanesulfonate | 286458-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-[(2S)-(E)-5-hydroxymethyl-4-methyl-3-penten-2-yl]tetrahydrofuran-2-methanol methanesulfonate
• CAS: 286458-75-1
• 化学式: C₁₄H₂₅BrO₅S
• 分子量: 385.319
• InChiKey: KQTHCHLGALMXPJ-YTRIMPNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-[(2S)-(E)-5-hydroxymethyl-4-methyl-3-penten-2-yl]tetrahydrofuran-2-methanol methanesulfonate 在 咪唑 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 癸烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 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：

  (αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-[(2S)-(E)-5-[((1,1-dimethyl)ethyl)dimethylsilyloxy]-4-methyl-3-penten-2-yl]tetrahydrofuran-2-methanol methanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(αR,2R,3S,4R)-3-bromo-2,4-dimethyl-α-[(2S)-(E)-5-hydroxymethyl-4-methyl-3-penten-2-yl]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