1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate | 528588-37-6

• 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: 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate
• 英文别名: 5-O-tert-butyl 1-O-methyl (2S,4S)-2-[(4-bromophenyl)methyl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS: 528588-37-6
• 化学式: C₂₂H₃₂BrNO₆
• 分子量: 486.403
• InChiKey: HEVZBDFOHUKWBN-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以74%的产率得到tert-butyl (2S,4S)-4-[(4-bromophenyl)methyl]-5-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
  参考文献：
  名称：

  Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

  摘要：

  A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02865-4
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate
  参考文献：
  名称：

  Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

  摘要：

  A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02865-4

文献信息

• 用于诊断和治疗的放射性谷氨酰胺衍生物及 其制备方法
  申请人：首都医科大学

  公开号：CN109369445B

  公开（公告）日：2021-10-15

  本发明公开了一种用于诊断和治疗的放射性谷氨酰胺衍生物及其制备方法，属于谷氨酰胺衍生物制备领域。本发明涉及：适合用被18F、123I、124I、125I或者131I标记的新型的谷氨酰胺衍生物及相应的经18F、123I、124I、125I或者131I标记的谷氨酰胺衍生物本身、其它们的经19F或127I类似物以及其它们作为参考标准的用途、制备此类化合物的方法、包含此类化合物的组合物、包含此类化合物或组合物的试剂盒以及此类化合物、组合物或试剂盒用于通过正电子发射断层造影正电子放射断层显像(PET)，或者单光子发射计算机断层成像术(SPECT)的诊断成像，或者131I治疗肿瘤的用途。
• Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues
  作者：Junyi Zhang、Wei Wang、Chiyi Xiong、Victor J. Hruby

  DOI：10.1016/s0040-4039(02)02865-4

  日期：2003.2

  A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.