tert-butyl (1S,2S)-2-((methoxycarbonyl)methylamino)cyclopentylcarbamate | 815645-23-9

• 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: tert-butyl (1S,2S)-2-((methoxycarbonyl)methylamino)cyclopentylcarbamate
• 英文别名: methyl 2-[[(1S,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentyl]amino]acetate
• CAS: 815645-23-9
• 化学式: C₁₃H₂₄N₂O₄
• 分子量: 272.345
• InChiKey: IWJWPZGVKAHXNX-UWVGGRQHSA-N

物化性质

• 熔点：
  49-52 °C
• 沸点：
  384.5±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S)-2-((methoxycarbonyl)methylamino)cyclopentylcarbamate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-(thymin-1-ylacetyl)glycine
  参考文献：
  名称：

  (S,S)-trans-Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity

  摘要：

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.

  DOI：

  10.1021/ja046280q
• 作为产物：
  描述：

  (1S,2s)-boc-2-氨基环戊烷羧酸 在 palladium on activated charcoal 氢气 、 氯甲酸乙酯 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 16.91h， 生成 tert-butyl (1S,2S)-2-((methoxycarbonyl)methylamino)cyclopentylcarbamate
  参考文献：
  名称：

  (S,S)-trans-Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity

  摘要：

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.

  DOI：

  10.1021/ja046280q

文献信息

• Synthesis of Fmoc-Protected (<i>S</i>,<i>S</i>)-<i>trans</i>-Cyclopentane Diamine Monomers Enables the Preparation and Study of Conformationally Restricted Peptide Nucleic Acids
  作者：Hongchao Zheng、Mrinmoy Saha、Daniel H. Appella

  DOI：10.1021/acs.orglett.8b03374

  日期：2018.12.7

  An efficient synthesis of Fmoc-protected (S,S)-trans-cyclopentane PNA (tcypPNA) monomers starting from mono-Boc-protected (S,S)-1,2-cyclopentanediamine is reported. A general synthetic strategy was developed so that tcypPNA monomers with each nucleobase can be made in sufficient quantity and purity for use in solid-phase peptide synthesis (SPPS). The newly synthesized monomers were then successfully

  报道了从单-Boc保护的（S，S）-1，2-环戊烷二胺开始的Fmoc保护的（S，S）-反-环戊烷PNA（tcyp PNA）单体的有效合成。已开发出通用的合成策略，以便可以制备具有每个核碱基的tcyp PNA单体，其数量和纯度足以用于固相肽合成（SPPS）。然后使用SPPS的标准Fmoc化学方法将新合成的单体成功地掺入10个残基的PNA低聚物中。不同的tcyp PNA允许序列中的不同位置在构象上受（S，S）-反式-环戊烷以确定对互补DNA结合的影响。