5-O-tert-butyl 1-O-methyl (2S,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpentanedioate | 528588-34-3

• 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: 5-O-tert-butyl 1-O-methyl (2S,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpentanedioate
• CAS: 528588-34-3
• 化学式: C₁₈H₃₁NO₆
• 分子量: 357.447
• InChiKey: DVJSDYJQOKHMNO-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  5-O-tert-butyl 1-O-methyl (2S,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpentanedioate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 28.0h， 生成 tert-butyl (2S,4S)-4-prop-2-enylpyrrolidine-2-carboxylate
  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 5-O-tert-butyl 1-O-methyl (2S,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpentanedioate
  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

• 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.