6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one | 124516-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one
• 英文别名: 2-methoxy-5-nitroso-6-<(β-D-2,3,4-tri-O-acetylxylopyranosyl)amino>pyrimidin-4(3H)-one；3,4-dihydro-3-methyl-2-methoxy-4-oxo-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)pyrimidine；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2-methoxy-1-methyl-5-nitroso-6-oxopyrimidin-4-yl)amino]oxan-2-yl]methyl acetate
• CAS: 124516-16-1
• 化学式: C₂₀H₂₆N₄O₁₂
• 分子量: 514.446
• InChiKey: HEBZJCVNJYBTLA-AEWXESQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one 在 sodium dithionite 、 氨 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.25h， 生成 6,7-dihydro-3-β-D-glucopyranosyl-6-methyl-5-methoxy-7-oxo-1,2,3-triazolo<4,5-d>pyrimidine
  参考文献：
  名称：

  4，5-二氨基，5-氨基-4-葡糖基氨基和4-氨基-5-葡糖基氨基嘧啶与亚硝酸反应。8-氮杂嘌呤的合成，抗癌和抗艾滋病作用†

  摘要：

  描述了4，5-二氨基，5-氨基-4-葡糖基氨基和4-氨基-5-葡糖基氨基嘧啶3a，3b，3c和4与亚硝酸的反应。已经获得了8-氮杂嘌呤7a，7c，8和N-亚硝基氨基衍生物5。对其中一些产品进行了抗癌和抗艾滋病活性测试。

  DOI：

  10.1002/jhet.5570280538

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。
• The Use of Formamidine Acetate in the Traube Synthesis of 9-Glycosylpurines
  作者：M. Melguizo、M. Nogueras、A. Sánchez

  DOI：10.1055/s-1992-26144

  日期：——

  Several 9-glycopyranosylpurin-6(1H)-one derivatives, where the glycosyl moiety was xylopyranosyl, glucopyranosyl 2,3,4,6-tetra-O-acetylglycopyranosyl, or 2,3,4-tri-O-xylopyranosyl, were obtained by reaction of formamidine acetate with 5-amino-6-(glycopyranosylamino)pyrimidin-4(3H)-ones or 5-amino-6-[(per-O-acetyl)glycopyranosyl]amino}pyrimidin-4(3H)-ones, respectively. The reaction conditions were mild, such that good yields, around 60%, were obtained.

  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。
• On the reaction of 6-glycosylamino-5-nitrosopyrimidines with vilsmeier-type reagents. Synthesis of 8-amino-9-glycosylpurines
  作者：M. Melguizo、M. Nogueras、A. Sanchez、Ma L. Quijano

  DOI：10.1016/s0040-4039(00)99094-4

  日期：1989.1
• 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.
• MELGUIZO, M.;NOGUERAS, M.;SANCHEZ, A.;QUIJANO, L., TETRAHEDRON LETT., 30,(1989) N0, C. 2669-2672
  作者：MELGUIZO, M.、NOGUERAS, M.、SANCHEZ, A.、QUIJANO, L.

  DOI：——

  日期：——