tert-butyl N-benzoyl-(S)-pyroglutamate | 454253-77-1

• 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: tert-butyl N-benzoyl-(S)-pyroglutamate
• 英文别名: tert-butyl (2S)-1-benzoyl-5-oxopyrrolidine-2-carboxylate
• CAS: 454253-77-1
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: FXUAWRMNHCISGX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-benzoyl-(S)-pyroglutamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到N-benzoyl-L-pyroglutamic acid
  参考文献：
  名称：

  A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries

  摘要：

  9-(S)-Pyroglutaminyl-beta-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00420-4
• 作为产物：
  描述：

  L-焦谷氨酸叔丁酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以74%的产率得到tert-butyl N-benzoyl-(S)-pyroglutamate
  参考文献：
  名称：

  A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries

  摘要：

  9-(S)-Pyroglutaminyl-beta-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00420-4

文献信息

• A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries
  作者：Takashi Itoh、Michiko Miyazaki、Sachiko Ikeda、Kazuhiro Nagata、Masashi Yokoya、Yuji Matsuya、Yasuko Enomoto、Akio Ohsawa

  DOI：10.1016/s0040-4020(03)00420-4

  日期：2003.5

  9-(S)-Pyroglutaminyl-beta-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products. (C) 2003 Elsevier Science Ltd. All rights reserved.