(L)-N-Boc-2-aminoadipic acid α-ethyl δ-4-methoxybenzyl ester

• 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: (L)-N-Boc-2-aminoadipic acid α-ethyl δ-4-methoxybenzyl ester
• 英文别名: 1-O-ethyl 6-O-[(4-methoxyphenyl)methyl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanedioate
• 化学式: C₂₁H₃₁NO₇
• 分子量: 409.48
• InChiKey: PCXISJZZNXWKCR-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-6-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 、 4-甲氧基苄醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(L)-N-Boc-2-aminoadipic acid α-ethyl δ-4-methoxybenzyl ester
  参考文献：
  名称：

  Regioselective ring opening of chiral N-Boc protected pyroglutamate and pyroaminoadipate ethyl esters with heteronucleophiles

  摘要：

  Mixed diesters, omega-amide and omega-thioesters are obtained from both N-Boc ethyl pyroglutamate and pyroaminoadipate under neutral or basic conditions.Under neutral conditions, the reaction is catalyzed by KCN and the use of Ultrasound speeds up the process. In basic conditions, reaction times are even shorter. In both cases, no transesterification of the alpha-ester was observed and the chirality of the alpha-amino acid was preserved.

  DOI：

  10.1016/s0040-4020(01)90232-7

文献信息

• Regioselective ring opening of chiral N-Boc protected pyroglutamate and pyroaminoadipate ethyl esters with heteronucleophiles
  作者：María Teresa Molina、Celestina del Valle、Ana María Escribano、Jesús Ezquerra、Concepción Pedregal

  DOI：10.1016/s0040-4020(01)90232-7

  日期：1993.4

  Mixed diesters, omega-amide and omega-thioesters are obtained from both N-Boc ethyl pyroglutamate and pyroaminoadipate under neutral or basic conditions.Under neutral conditions, the reaction is catalyzed by KCN and the use of Ultrasound speeds up the process. In basic conditions, reaction times are even shorter. In both cases, no transesterification of the alpha-ester was observed and the chirality of the alpha-amino acid was preserved.