(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester | 132592-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester
• CAS: 132592-40-6
• 化学式: C₁₂H₂₃NO₆Si
• 分子量: 305.403
• InChiKey: WYXDEGQQAXMEHZ-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107.3
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(4S,5R)-4-羟基-5-(羟基甲基)-L-脯氨酸
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040
• 作为产物：
  描述：

  (5R,4S,2S)-4-acetoxy-5-hydroxymethyl-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以72%的产率得到(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040