(2S,4S)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) | 132591-97-0

• 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)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)
• 英文别名: dibenzyl (2S,4S)-4-(2,2-dimethylpropanoyloxy)pyrrolidine-1,2-dicarboxylate
• CAS: 132591-97-0
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: SMOGTMNUZXOMOK-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,4S)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 在 四乙基对甲苯磺酸铵 作用下， 反应 2.0h， 以10%的产率得到(2S,4S,5RS)-5-methoxy-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl 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
• 作为产物：
  描述：

  (2s,4r)-1,2-二苄氧羰基-4-羟基吡咯烷 在 4-二甲氨基吡啶 、 lithium benzyloxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯甲醇 为溶剂， 反应 17.5h， 生成 (2S,4S)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl 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