methyl (S)-(1-(((benzyloxy)carbonyl)amino)propan-2-yl)glycinate | 1350821-72-5

• 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: methyl (S)-(1-(((benzyloxy)carbonyl)amino)propan-2-yl)glycinate
• CAS: 1350821-72-5
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: BZAVWXQXUUSEBA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-(1-(((benzyloxy)carbonyl)amino)propan-2-yl)glycinate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成 (S)-2-(N-(1-(((Benzyloxy)carbonyl)amino)propan-2-yl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid
  参考文献：
  名称：

  β-PNA: Peptide nucleic acid (PNA) with a chiral center at the β-position of the PNA backbone

  摘要：

  Peptide nucleic acid (PNA) monomers with a methyl group at the beta-position have been synthesized. The modified monomers were incorporated into PNA oligomers using Fmoc chemistry for solid-phase synthesis. Thermal denaturation and circular dichroism (CD) studies have shown that PNA containing the S-form monomers was well suited to form a hybrid duplex with DNA, whose stability was comparable to that of unmodified PNA-DNA duplex, whereas PNA containing the R-form monomers was not. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.017
• 作为产物：
  描述：

  (S)-1,2-diaminopropane 、 碳酸苄基苯酯 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 39.0h， 以77%的产率得到methyl (S)-(1-(((benzyloxy)carbonyl)amino)propan-2-yl)glycinate
  参考文献：
  名称：

  β-PNA: Peptide nucleic acid (PNA) with a chiral center at the β-position of the PNA backbone

  摘要：

  Peptide nucleic acid (PNA) monomers with a methyl group at the beta-position have been synthesized. The modified monomers were incorporated into PNA oligomers using Fmoc chemistry for solid-phase synthesis. Thermal denaturation and circular dichroism (CD) studies have shown that PNA containing the S-form monomers was well suited to form a hybrid duplex with DNA, whose stability was comparable to that of unmodified PNA-DNA duplex, whereas PNA containing the R-form monomers was not. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.017