[(S)-3-(4-Allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-propoxy]-acetic acid tert-butyl ester | 191655-51-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(S)-3-(4-Allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-propoxy]-acetic acid tert-butyl ester
• CAS: 191655-51-3
• 化学式: C₂₂H₃₄N₄O₈
• 分子量: 482.534
• InChiKey: HXVPLSGHGOBBAV-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  147.08
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(S)-3-(4-Allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-propoxy]-acetic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 0.5h， 以75%的产率得到[(S)-3-(4-Allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-amino-propoxy]-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：

  N-BOC-O-苄基-L-丝氨酸 在 palladium on activated charcoal 吡啶 、 1H-1,2,4-三唑 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 四丁基硫酸氢铵 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 、 三氯氧磷 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 15.0h， 生成 [(S)-3-(4-Allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-propoxy]-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