[(S)-2-tert-Butoxycarbonylamino-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid | 191655-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [(S)-2-tert-Butoxycarbonylamino-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid
• CAS: 191655-64-8
• 化学式: C₁₆H₂₅N₃O₇
• 分子量: 371.39
• InChiKey: RRDWHHQLLBJIMS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  139.72
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(S)-2-tert-Butoxycarbonylamino-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.5h， 生成 7-(thymin-1-yl)-5S-[N-(fluoren-9-ylmethoxycarbonyl)amino]-3-oxaheptanoic acid
  参考文献：
  名称：

  Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

  摘要：

  Nucleoamino acids of type I - III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side chains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil --> cytosine base conversion at the stage of N-delta-BOC protected amino acid tert-butyl esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00172-8
• 作为产物：
  描述：

  tert-butyl 7-hydroxy-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 [(S)-2-tert-Butoxycarbonylamino-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid
  参考文献：
  名称：

  Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

  摘要：

  Nucleoamino acids of type I - III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side chains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil --> cytosine base conversion at the stage of N-delta-BOC protected amino acid tert-butyl esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00172-8