Acetic acid (2R,5S)-5-benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl ester | 441019-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (2R,5S)-5-benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl ester
• 英文别名: [(2R,5S)-5-ethoxy-5-(phenylmethoxymethyl)-2H-furan-2-yl] acetate
• CAS: 441019-86-9
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: BKVKZZWFLOKSOL-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,5S)-5-benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl ester 在 N,O-双三甲硅基乙酰胺 、 zinc diacetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 1-((S)-5-Benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Asymmetric Synthesis of 4‘-Ethoxy-2‘,3‘-didehydro-2‘,3‘-dideoxynucleosides by Palladium-Catalyzed Kinetic Discrimination between the Corresponding Diastereoisomeric Lactol Acetates

  摘要：

  4'-Substituted nucleoside analogues have been synthesized using palladium-catalyzed asymmetric allylic amination conditions. A kinetic discrimination between the diastereomeric lactol acetates (3) produced the desired aminated products (6a-d) and recovered acetate (alpha-3) in high yields and <97:3 diastereoselectivity. Epimerization of the recovered lactol acetate (alpha-3) produced a 60:40 alpha/beta mixture of (3), which could be resubjected, in principle, to the palladium-catalyzed asymmetric allylic amination conditions.

  DOI：

  10.1021/jo011074b
• 作为产物：
  描述：

  胸腺嘧啶 、 (5S)-2-acetoxy-5-(benzyloxymethyl)-5-ethoxy-2,5-dihydrofuran 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N,O-双三甲硅基乙酰胺 、 (S,S)-DACH-phenyl Trost ligand 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 生成 Acetic acid (2R,5S)-5-benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl ester 、 Acetic acid (2S,5S)-5-benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl ester 、 1-((2S,5S)-5-Benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 、 1-((2R,5S)-5-Benzyloxymethyl-5-ethoxy-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Asymmetric Synthesis of 4‘-Ethoxy-2‘,3‘-didehydro-2‘,3‘-dideoxynucleosides by Palladium-Catalyzed Kinetic Discrimination between the Corresponding Diastereoisomeric Lactol Acetates

  摘要：

  4'-Substituted nucleoside analogues have been synthesized using palladium-catalyzed asymmetric allylic amination conditions. A kinetic discrimination between the diastereomeric lactol acetates (3) produced the desired aminated products (6a-d) and recovered acetate (alpha-3) in high yields and <97:3 diastereoselectivity. Epimerization of the recovered lactol acetate (alpha-3) produced a 60:40 alpha/beta mixture of (3), which could be resubjected, in principle, to the palladium-catalyzed asymmetric allylic amination conditions.

  DOI：

  10.1021/jo011074b