(S)-5-<(tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone | 156604-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-5-<(tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone
• 英文别名: tert-butyl (2S)-2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-5-oxopyrrolidine-1-carboxylate
• CAS: 156604-26-1
• 化学式: C₁₅H₂₆N₂O₅
• 分子量: 314.382
• InChiKey: AYBSLJPSDJCTEV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-<(tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone 在 lithium hydroxide 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 19.0h， 生成 (2S)-N¹,N²-di-tert-butoxycarbonyl-1,2,4-triaminobutane
  参考文献：
  名称：

  Selectively protected chiral 1,2,4-triaminobutanes and chiral vicinal 1,2-diamines

  摘要：

  Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to mono-, di- and triacylated compounds has been elaborated. Ring opening of (S)-5-(Boc-aminomethyl)-N-1-Boc-2-pyrrolidone with LiOH afforded the Boc-protected 4,5-diaminovaleric acid, whereas with NaBH4 the Boc-protected (S)4,5-diamino-pentanol was obtained The acid underwent Curtius rearrangement to the corresponding isocyanate which was transformed to (S)-N-1,N-2-di-Boc-1,2,4-triaminobutane and to N-1,N-2-di-Boc-N-4-Z-triaminobutane. Curtius rearrangement of (S)-N-4,N-5-di-Z-valeric acid and pTSA catalyzed addition of t-BuOH to the isocyanate, yielded N-1,N-2-di-Z-N-4-Boc-1,2,4-triaminobutane.

  DOI：

  10.1016/s0957-4166(00)86240-0
• 作为产物：
  描述：

  (S)-5-氨基甲基-2-吡咯烷酮 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 生成 (S)-5-<(tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone
  参考文献：
  名称：

  Selectively protected chiral 1,2,4-triaminobutanes and chiral vicinal 1,2-diamines

  摘要：

  Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to mono-, di- and triacylated compounds has been elaborated. Ring opening of (S)-5-(Boc-aminomethyl)-N-1-Boc-2-pyrrolidone with LiOH afforded the Boc-protected 4,5-diaminovaleric acid, whereas with NaBH4 the Boc-protected (S)4,5-diamino-pentanol was obtained The acid underwent Curtius rearrangement to the corresponding isocyanate which was transformed to (S)-N-1,N-2-di-Boc-1,2,4-triaminobutane and to N-1,N-2-di-Boc-N-4-Z-triaminobutane. Curtius rearrangement of (S)-N-4,N-5-di-Z-valeric acid and pTSA catalyzed addition of t-BuOH to the isocyanate, yielded N-1,N-2-di-Z-N-4-Boc-1,2,4-triaminobutane.

  DOI：

  10.1016/s0957-4166(00)86240-0

文献信息

• LINKER-DRUG AND ANTIBODY-DRUG CONJUGATE (ADC) EMPLOYING THE SAME
  申请人：Industrial Technology Research Institute

  公开号：US20180169262A1

  公开（公告）日：2018-06-21

  A linker-drug represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof is provided. In formula (I), C is a conjugator, L is a linker unit, D is a toxin unit, and n is an integer ranging from 1 to 4. The structure of the conjugator is represented by formula (II). In formula (II), X is a leaving group, each of R 1 and R 2 is independently a single bond or —NH—, and Z is substituted aryl, heteroaryl, linear alkyl, cycloalkyl, heterocycloalkyl, or a combination thereof. The antibody is conjugated to the linker unit through a cysteine residue of the antibody. An antibody-drug conjugate (ADC) employing the above linker-drug is also provided.

  提供由式（I）表示的连接药物或其药学上可接受的盐或溶剂。在式（I）中，C是一个结合物，L是一个连接单元，D是一个毒素单元，n是一个从1到4的整数。结合物的结构由式（II）表示。在式（II）中，X是一个离去基团，R1和R2中的每一个独立地是一个单键或—NH—，Z是取代芳基、杂环芳基、直链烷基、环烷基、杂环烷基或它们的组合。抗体通过抗体的半胱氨酸残基与连接单元结合。还提供了使用上述连接药物的抗体-药物结合物（ADC）。
• Selectively protected chiral 1,2,4-triaminobutanes and chiral vicinal 1,2-diamines
  作者：Janina Altman、Dov Ben-Ishai、Wolfgang Beck

  DOI：10.1016/s0957-4166(00)86240-0

  日期：1994.5

  Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to mono-, di- and triacylated compounds has been elaborated. Ring opening of (S)-5-(Boc-aminomethyl)-N-1-Boc-2-pyrrolidone with LiOH afforded the Boc-protected 4,5-diaminovaleric acid, whereas with NaBH4 the Boc-protected (S)4,5-diamino-pentanol was obtained The acid underwent Curtius rearrangement to the corresponding isocyanate which was transformed to (S)-N-1,N-2-di-Boc-1,2,4-triaminobutane and to N-1,N-2-di-Boc-N-4-Z-triaminobutane. Curtius rearrangement of (S)-N-4,N-5-di-Z-valeric acid and pTSA catalyzed addition of t-BuOH to the isocyanate, yielded N-1,N-2-di-Z-N-4-Boc-1,2,4-triaminobutane.