6-<<β-D-(Tri-O-acetyl)xylopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one | 125172-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-<<β-D-(Tri-O-acetyl)xylopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one
• 英文别名: 2-methoxy-3-methyl-5-nitroso-6-(2,3,5-tri-O-acetyl-β-D-xylopyranosylamino)pyrimidin-4-(3H)-one；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2-methoxy-1-methyl-5-nitroso-6-oxopyrimidin-4-yl)amino]oxan-3-yl] acetate
• CAS: 125172-02-3
• 化学式: C₁₇H₂₂N₄O₁₀
• 分子量: 442.382
• InChiKey: MVLJOYVOQPVMDT-CQROYNQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-<<β-D-(Tri-O-acetyl)xylopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one 在 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以60%的产率得到Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(5-amino-2-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-4-ylamino)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The Use of Formamidine Acetate in the Traube Synthesis of 9-Glycosylpurines

  摘要：

  获得了几种9-吡喃糖基嘌呤-6(1H)-酮衍生物，其中糖基部分是吡喃木糖基、吡喃葡萄糖基2,3,4,6-四-O-乙酰基吡喃糖基或2,3,4-三-O-吡喃木糖基通过乙酸甲脒与分别为5-氨基-6-(吡喃糖基氨基)嘧啶-4(3H)-酮或5-氨基-6-{[(全-O-乙酰基)吡喃糖基]氨基}嘧啶-4(3H)-酮。反应条件温和，收率良好，可达60%左右。

  DOI：

  10.1055/s-1992-26144

文献信息

• Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5-nitroso
  作者：Group M. Melguizo、A. Marchal、M. Nogueras、A. Sánchez、J. N. Low

  DOI：10.1002/jhet.5570390114

  日期：2002.1

  The nucleophilic substitution of 2-mefhoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5-nitroso group on to the pyrimidine ring. The aminolysis of several 2-methoxy-5-nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non-hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates

  通过在嘧啶环上引入5-亚硝基将强烈激活嘧啶衍生物中2-甲氧基的亲核取代。几种2-甲氧基-5-亚硝基嘧啶衍生物的氨解反应可在室温下在羟基以及具有不同伯胺的非羟基介质中进行，且时间短且收率高。氨基裂解的底物包括6-[[（- O-乙酰基）糖基]氨基嘧啶，其提供相应的2-氨基嘧啶而不损害糖部分的乙酰基保护基。
• A new one-step synthesis of 8-aminopurine nucleoside analogs from 6-(glycosylamino)-5-nitrosopyrimidines
  作者：Manuel Melguizo、Manuel Nogueras、Adolfo Sanchez

  DOI：10.1021/jo00028a031

  日期：1992.1

  The reaction of 6-[[beta-D-(per-O-acetyl)glycopyranosyl]amino]-5-nitrosopyrimidines (1) with POCl3/formamide furnished 8-amino-9-[(per-O-acetyl)glycopyranosyl]purines (2) in good yield. In this reaction formamide seems to play a double role, as the source of the C(8)-amino group of the purine and as the agent responsible for the reduction of the C(5)-nitroso group of the pyrimidine to a hydroxylamino group. A mechanism which reflects this belief is presented. Chemical evidence that supports the mechanism is provided.