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