tert-butyl (2S,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate | 191280-89-4

• 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: tert-butyl (2S,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate
• CAS: 191280-89-4
• 化学式: C₁₂H₂₃NO₈S₂
• 分子量: 373.449
• InChiKey: DFSNHEWREAAHBX-UWVGGRQHSA-N

物化性质

• 沸点：
  551.6±43.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4R)-2-[N,N-bis(2-cyanoethyl)aminomethyl]-4-[N,N-bis(2-cyanoethyl)amino]-N1-(2-cyanoethyl)pyrrolidine
  参考文献：
  名称：

  吡咯烷基多胺：稳定DNA双链体和三链体的支链手性多胺类似物。

  摘要：

  吡咯烷基多胺（III-VI）是构象受限的线性精胺的手性类似物，可通过添加氨基丙基链进行精细修饰以产生支链非对映异构体。已经证明，在低至0.01 mM的浓度下，这些化合物通过强的静电相互作用可显着稳定DNA双链体和三链体。合成的化合物是具有手性吡咯烷核的潜在树突，此类分子可能具有作为DNA传递和转染剂的潜力。

  DOI：

  10.1021/ol006822i
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 锂硼氢 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 70.0h， 生成 tert-butyl (2S,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability

  摘要：

  The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA tripler than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.

  DOI：

  10.1021/jo970414j

文献信息

• Conformationally Restrained Chiral Analogues of Spermine:  Chemical Synthesis and Improvements in DNA Triplex Stability
  作者：Kallanthottathil G. Rajeev、Gangadhar J. Sanjayan、Krishna N. Ganesh

  DOI：10.1021/jo970414j

  日期：1997.7.1

  The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone to effect conformational rigidity, with simultaneous creation of two asymmetric centers. The chiral analogues bind both AT and CG rich DNA duplexes as effectively as spermine and exhibit even better association with DNA tripler than spermine. The newer analogues have features for structural elaboration to novel molecular entities of potential importance in therapeutics and material design.
• Pyrrolidyl Polyamines:  Branched, Chiral Polyamine Analogues That Stabilize DNA Duplexes and Triplexes
  作者：Dendukuri Nagamani、Krishna N. Ganesh

  DOI：10.1021/ol006822i

  日期：2001.1.1

  linear spermine elaborated by the addition of aminopropyl chains to yield branched diastereomers. It is demonstrated that in concentrations as low as 0.01 mM, these compounds remarkably stabilize DNA duplexes and triplexes through strong electrostatic interactions. The synthesized compounds are potential dendrons with a chiral pyrrolidine core, and such molecules may have potential as DNA delivery and

  吡咯烷基多胺（III-VI）是构象受限的线性精胺的手性类似物，可通过添加氨基丙基链进行精细修饰以产生支链非对映异构体。已经证明，在低至0.01 mM的浓度下，这些化合物通过强的静电相互作用可显着稳定DNA双链体和三链体。合成的化合物是具有手性吡咯烷核的潜在树突，此类分子可能具有作为DNA传递和转染剂的潜力。