tert-butyl 3(S)-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)butanoate | 220542-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3(S)-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)butanoate
• 英文别名: tert-butyl (3S)-4-(4-methylphenyl)sulfonyloxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 220542-06-3
• 化学式: C₂₀H₃₁NO₇S
• 分子量: 429.535
• InChiKey: MGPLXDCYSXPIJI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氰化钠 、 tert-butyl 3(S)-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)butanoate 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  新组成部分的合成：走向肽核酸（PNA）的类似物

  摘要：

  为了获得肽核酸（PNA）的新类似物，已经实现了构件14的合成。结构单元14已经从异硫氰酸酯衍生物12与13的偶合中得到。从S-天冬氨酸衍生物5通过许多步骤获得异硫氰酸酯衍生物12。

  DOI：

  10.1016/s0040-4039(98)01007-7
• 作为产物：
  描述：

  BOC-L-天门冬氨酸4-叔丁基-1-羟基-琥珀酰亚胺酯 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 tert-butyl 3(S)-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)butanoate
  参考文献：
  名称：

  Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators

  摘要：

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.

  DOI：

  10.1021/jm980340j

文献信息

• Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators
  作者：Raymond J. Bergeron、Jan Wiegand、William R. Weimar、J. R. Timothy Vinson、Jörg Bussenius、Guo Wei Yao、James S. McManis

  DOI：10.1021/jm980340j

  日期：1999.1.1

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
• Synthesis of new building blocks: Towards the analogs of peptide nucleic acids (PNAs)
  作者：Carol Dallaire、Prabhat Arya

  DOI：10.1016/s0040-4039(98)01007-7

  日期：1998.7

  To obtain new analogs of peptide nucleic acids (PNAs), synthesis of the building block 14 has been achieved. Building block 14 has been derived from the coupling of the isothiocyanate derivative, 12 with 13. Isothiocyanate derivative 12 was obtained from S-aspartic acid derivative 5 in a number of steps.

  为了获得肽核酸（PNA）的新类似物，已经实现了构件14的合成。结构单元14已经从异硫氰酸酯衍生物12与13的偶合中得到。从S-天冬氨酸衍生物5通过许多步骤获得异硫氰酸酯衍生物12。