3'-amino-5'-ethoxycarbonylamino-2',3',5'-trideoxyuridine

• 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: 3'-amino-5'-ethoxycarbonylamino-2',3',5'-trideoxyuridine
• 英文别名: ethyl N-[[(2R,3S,5R)-3-amino-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]carbamate
• 化学式: C₁₂H₁₈N₄O₅
• 分子量: 298.299
• InChiKey: LTROABFRPPFGIE-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3',5'-diamino-2',3',5'-trideoxyuridine 、 碳酸二乙酯 在 吡啶 、 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以67%的产率得到3'-amino-5'-ethoxycarbonylamino-2',3',5'-trideoxyuridine
  参考文献：
  名称：

  First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues

  摘要：

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.

  DOI：

  10.1021/jo035678m

文献信息

• First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues
  作者：Iván Lavandera、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/jo035678m

  日期：2004.3.1

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.