(2S,4R)-4-(4-Chloro-naphthalen-1-yloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 367966-46-9

• 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,4R)-4-(4-Chloro-naphthalen-1-yloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S,4R)-4-(4-chloronaphthalen-1-yl)oxy-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 367966-46-9
• 化学式: C₂₁H₂₂ClNO₆
• 分子量: 419.862
• InChiKey: ZIBDNVOQMOUZAQ-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2S,4R)-4-(4-Chloro-naphthalen-1-yloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2S,4R)-5-Acetoxy-4-(4-chloro-naphthalen-1-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  A convenient and high yield method to prepare 4-hydroxypyroglutamic acids

  摘要：

  RuO2/NaIO4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivates in high yields. Desilylation with TBAF afforded both cis- and trans-N-Boc-methyl-4-hydroxy pyroglutamates. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01030-9
• 作为产物：
  描述：

  1-(叔丁基)-2-甲基(2S,4S)-4-((叔丁基二甲基甲硅烷基)氧基)-5-氧代吡咯烷-1,2-二羧酸酯 在 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4R)-4-(4-Chloro-naphthalen-1-yloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  A convenient and high yield method to prepare 4-hydroxypyroglutamic acids

  摘要：

  RuO2/NaIO4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivates in high yields. Desilylation with TBAF afforded both cis- and trans-N-Boc-methyl-4-hydroxy pyroglutamates. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01030-9

文献信息

• A convenient and high yield method to prepare 4-hydroxypyroglutamic acids
  作者：Xiaojun Zhang、Aaron C. Schmitt、Wen Jiang

  DOI：10.1016/s0040-4039(01)01030-9

  日期：2001.8

  RuO2/NaIO4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivates in high yields. Desilylation with TBAF afforded both cis- and trans-N-Boc-methyl-4-hydroxy pyroglutamates. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.