cis-4-benzyloxy-2,3-epoxybutanoic acid

• 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: cis-4-benzyloxy-2,3-epoxybutanoic acid
• 英文别名: (2S,3S)-3-(phenylmethoxymethyl)oxirane-2-carboxylic acid
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: ROQMIBFIURLEJR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4-benzyloxy-2,3-epoxybutanoic acid 在 sodium azide 、 magnesium(II) perchlorate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 18.0h， 生成 methyl syn-3-azido-4-benzyloxy-2-hydroxybutanoate
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters

  摘要：

  The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)].

  DOI：

  10.1016/0040-4020(95)00877-b
• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 ruthenium trichloride 、 高碘酸 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 cis-4-benzyloxy-2,3-epoxybutanoic acid
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters

  摘要：

  The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)].

  DOI：

  10.1016/0040-4020(95)00877-b

文献信息

• Diastereo- and Enantioselective Synthesis of Fluorinated Threonines
  作者：Carlo Scolastico、Esterino Conca、Laura Prati、Giuseppe Guanti、Luca Banfi、Adriano Berti、Paolo Farina、Umberto Valcavi

  DOI：10.1055/s-1985-31363

  日期：——

  (d,l)-threo and allo-2-amino-4,4,4-trifluoro-3-hydroxybutanoic acids are synthesised from ethyl trifluoroacetoacetate via reduction and saponification of the 4,4,4-trifluoro-3-hydroxy-2-methoxyiminobutanoate. threo-Isomers are stereospecifically obtained by epimerisation of allo-isomers via the corresponding oxazolidinones. An acylation and stereoselective reduction sequence performed on ethyl N,N-dibenzylaminoacetate also leads to threo-isomers (1A) in good yields. An enantioselective synthesis of (L)-4-fluorothreonine by regiospecific opening of (2S), (3R)-3-benzyloxyoxiranecarboxylic acid is reported.

  (d,l)-threo和allo-2-氨基-4,4,4-三氟-3-羟基丁酸是通过乙基三氟乙酰乙酸酯的还原和水解4,4,4-三氟-3-羟基-2-甲氧基亚氨基丁酸酯来合成的。通过相应的唑烷酮的差向异构化可以立体特异性地获得threo异构体。在乙基N,N-二苄基氨基乙酸酯上进行的酰化和立体选择性还原序列也能以良好的产率得到threo异构体(1A)。报道了一种通过(2S),(3R)-3-苄氧基环氧乙烷羧酸的区域特异性开环来选择性合成(L)-4-氟苏氨酸的方法。
• US5190969A
  申请人：——

  公开号：US5190969A

  公开（公告）日：1993-03-02
• US6153589A
  申请人：——

  公开号：US6153589A

  公开（公告）日：2000-11-28