(+)-[(5R,6S,Ss)-6-amino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate | 675124-88-6

• 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: (+)-[(5R,6S,Ss)-6-amino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate
• 英文别名: methyl (2S,3R)-2-amino-3-[[(S)-(4-methylphenyl)sulfinyl]amino]-7-(4-methylphenyl)sulfonyloxyheptanoate
• CAS: 675124-88-6
• 化学式: C₂₂H₃₀N₂O₆S₂
• 分子量: 482.622
• InChiKey: QLABTQPQDHJPSG-ICYRDHFCSA-N

物化性质

• 沸点：
  662.7±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)-[(5R,6S,Ss)-6-amino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate 在 sodium hydroxide 、 磷酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 (-)-methyl (2S)-[2-benzyloxycarbonylamino-2-piperidin-(2'R)-yl]acetate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j
• 作为产物：
  描述：

  (+)-methyl [(2S,4R,5S,Ss)-2-phenyl-1-(p-tolylsulfinyl)-5-[4-(toluenesulfonyloxy)butyl]-1,3-imidazolidin-4-yl]carboxylate 在 磷酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以68%的产率得到(+)-[(5R,6S,Ss)-6-amino-6-(methoxycarbonyl)-5-(p-tolylsulfinylamino)]hexyl p-tolylsulfonate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j

文献信息

• Synthesis of enantiopure vicinal diaminoesters and ketopiperazines from N-sulfinylimidazolidines
  作者：Alma Viso、Roberto Fernández de la Pradilla、Aída Flores、Ana García

  DOI：10.1016/j.tet.2007.05.062

  日期：2007.8

  A short and efficient synthesis of mono- and bicyclic ketopiperazines bearing methoxycarbonyl substituents is described. The route entails selective protection and solvolysis of N-sulfinylimidazolidines to provide vicinal diaminoesters with the nitrogen atoms suitably differentiated. Then, an N-acylation/cyclization protocol renders the ketopiperazines. In addition a diastereoselective route to an

  描述了带有甲氧基羰基取代基的单环和双环酮哌嗪的短而有效的合成。该途径需要对N-亚磺酰亚胺基咪唑烷进行选择性保护和溶剂分解，以提供具有适当区分的氮原子的邻二氨基酯。然后，N-酰化/环化方案产生了酮哌嗪。另外，描述了通过该方法可获得的通过2-哌啶基甘氨酸酯到天然二酮哌嗪DKP 593A类似物的非对映选择性途径。