3-methyl-2-methylthio-6-(tetra-O-acetyl-β-D-glucopyranosylamino)pyrimidin-4(3H)-one | 94940-17-7

• 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: 3-methyl-2-methylthio-6-(tetra-O-acetyl-β-D-glucopyranosylamino)pyrimidin-4(3H)-one
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1-methyl-2-methylsulfanyl-6-oxopyrimidin-4-yl)amino]oxan-2-yl]methyl acetate
• CAS: 94940-17-7
• 化学式: C₂₀H₂₇N₃O₁₀S
• 分子量: 501.514
• InChiKey: KZCUPCTYPRMQAY-LQDZTQBFSA-N

物化性质

• 沸点：
  582.3±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  34
• 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：
  184
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-methyl-2-methylthio-6-(tetra-O-acetyl-β-D-glucopyranosylamino)pyrimidin-4(3H)-one 在 亚硝酸异戊酯 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以90%的产率得到6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-(methylthio)-5-nitrosopyrimidin-4(3H)-one
  参考文献：
  名称：

  Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. Scope and Synthetic Applications

  摘要：

  描述了一种新颖简单的方法，该方法基于在无任何添加酸的DMSO中用异戊醇硝酸酯（IAN）处理，实现对氨基嘧啶衍生物的选择性C(5)-亚硝化。该方法证明适合于多克级规模，并且适用于比之前已知程序更广泛的嘧啶衍生物，包括氨基-二烷氧基嘧啶。分析了其适用范围，并展示了一些新制备物作为潜在生物兴趣的融合杂环衍生物合成中的中间体的实用性示例。

  DOI：

  10.1055/s-2002-19760

文献信息

• Aminopyrimidines and derivatives. XXI. Synthesis of 5-acyl-(4-.BETA.-d-glycopyranosylamino)pyrimidine derivatives as potential anticancer agents.
  作者：JACINTO NEGRILLO、MANUEL NOGUERAS、ADOLFO SANCHEZ、MIGUEL MELGAREJO

  DOI：10.1248/cpb.36.386

  日期：——

  Acetylation of 4-(O-acetyl-β-D-glycopyranosylamino)-6-oxo-pyrimidines (2a, d, e) with Ac2O/pyridine at 80°C gave the 6-acetoxy derivatives 3a, d, e. Although these were also obtained by treatment with Ac2O/H2SO4, prolonged reactions of 2a-c, e-f gave the 5-acetyl derivatives 4a-c, e-f. The Vilsmeier reaction of 2b-g produced the 5-formyl derivatives 5b-g, whereas 2a gave the uracil derivative 9 under similar conditions.

  4-(O-乙酰基-β-D-吡喃糖基氨基)-6-氧代-嘧啶(2a,d,e)在80℃下用Ac2O/吡啶乙酰化得到6-乙酰氧基衍生物3a,d,e。虽然这些也是通过用 Ac2O/H2SO4 处理获得的，但 2a-c、e-f 的延长反应得到 5-乙酰基衍生物 4a-c、e-f。 2b-g的Vilsmeier反应产生5-甲酰基衍生物5b-g，而2a在类似条件下产生尿嘧啶衍生物9。
• A new method for the synthesis of 2-glycosylamino pyridines
  作者：Justo Cobo、Manuel Melguizo、Adolfo Sa´nchez、Manuel Nogueras、Erik De Clercq

  DOI：10.1016/0040-4020(96)00214-1

  日期：1996.4

  tandem Diels-Alder/Retro Diels-Alder (DA/RDA) reaction starting from 6-glycosylaminopyrimidines, 6, with dimethyl acetylenedicarboxylate (DMAD) as dienophile. This approach represents a new method for the synthesis of 2-aminopyridine nucleoside analogues. The compounds were tested for their antiviral activity but did not prove active.

  几个2- glycosylaminopyridines 7，是通过串联狄尔斯-阿尔德/逆狄尔斯-阿尔德（DA / RDA）反应从6- glycosylaminopyrimidines，开始合成6，用二甲基乙炔（DMAD）作为亲二烯体。这种方法代表了一种合成2-氨基吡啶核苷类似物的新方法。测试了这些化合物的抗病毒活性，但未证明具有活性。
• Reaction of 6-glycopyranosylaminopyrimidin-4-ones with malonic acids. Synthesis of 8-glycopyranosylpyrido[2,3-d]pyrimidin-4-one derivatives
  作者：Luisa Quijano、Manuel Nogueras、Miguel Melgarejo、Adolfo S�nchez

  DOI：10.1007/bf00810825

  日期：1991.4

  Reactions of 6-glycopyranosylaminopyrimidin-4-ones 1 a-d with malonic, methyl malonic and ethyl malonic acids are discussed in this paper. These reactions have been carried out in acetic anhydride at 100-degrees-C affording the 8-glycopyranosylpyrido[2,3-d]pyrimidin-4-ones 2 a-d, 3 c-d and the 5-acyl-6-glycopyranosylaminopyrimidin-6-ones 4 a-d, 5 a-d.
• García; Melguizo; Cobo, Synlett, 2001, # 1, p. 57 - 60
  作者：García、Melguizo、Cobo、Sánchez、Nogueras、López、Low

  DOI：——

  日期：——
• Garcia, Jose A.; Sanchez, Adolfo; Nogueras, Manuel, Heterocycles, 1988, vol. 27, # 10, p. 2439 - 2442
  作者：Garcia, Jose A.、Sanchez, Adolfo、Nogueras, Manuel

  DOI：——

  日期：——