[(S)-2-tert-Butoxycarbonylamino-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid tert-butyl ester | 191655-66-0

• 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-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid tert-butyl ester
• CAS: 191655-66-0
• 化学式: C₁₉H₃₁N₃O₇
• 分子量: 413.471
• InChiKey: FNIZIXNVWZEONI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  128.72
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(S)-2-tert-Butoxycarbonylamino-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid tert-butyl ester 在 1H-1,2,4-三唑 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 [(S)-2-Amino-4-(4-benzyloxycarbonylamino-2-oxo-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
• 作为产物：
  描述：

  tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以86%的产率得到[(S)-2-tert-Butoxycarbonylamino-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butoxy]-acetic acid tert-butyl ester
  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