(1S,2S)-tert-Butyl 1--2-<<<(methylthio)(toluenesulfonylimido)methyl>amino>methyl>cyclopropane-1-carboxylate | 154704-05-9

• 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: (1S,2S)-tert-Butyl 1--2-<<<(methylthio)(toluenesulfonylimido)methyl>amino>methyl>cyclopropane-1-carboxylate
• 英文别名: (1S,2S)-tert-Butyl 1-[N-(tert-butoxycarbonyl)amino]-2-({[(methylthio)(toluenesulfonylimido)methyl]amino}methyl)cyclopropane-1-carboxylate；tert-butyl (1S,2S)-2-[[[[(4-methylphenyl)sulfonylamino]-methylsulfanylmethylidene]amino]methyl]-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 154704-05-9
• 化学式: C₂₃H₃₅N₃O₆S₂
• 分子量: 513.679
• InChiKey: AWXUAQADNICFRW-HJPURHCSSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2S)-tert-Butyl 1--2-<<<(methylthio)(toluenesulfonylimido)methyl>amino>methyl>cyclopropane-1-carboxylate 在 氨 、 silver nitrate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (1S,2S)-1-amino-2-[[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]methyl]cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039
• 作为产物：
  描述：

  tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 32.0h， 生成 (1S,2S)-tert-Butyl 1--2-<<<(methylthio)(toluenesulfonylimido)methyl>amino>methyl>cyclopropane-1-carboxylate
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039

文献信息

• Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine
  作者：Kevin Burgess、Dongyeol Lim、Kwok-Kan Ho、Chun-Yen Ke

  DOI：10.1021/jo00087a039

  日期：1994.4

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.