6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-(methylthio)-5-nitrosopyrimidin-4(3H)-one | 125162-92-7

• 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: 6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-(methylthio)-5-nitrosopyrimidin-4(3H)-one
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1-methyl-2-methylsulfanyl-5-nitroso-6-oxopyrimidin-4-yl)amino]oxan-2-yl]methyl acetate
• CAS: 125162-92-7
• 化学式: C₂₀H₂₆N₄O₁₁S
• 分子量: 530.513
• InChiKey: OXTZKSYMURNXGL-AEWXESQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  214
• 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-(methylthio)-5-nitrosopyrimidin-4(3H)-one 、 formamide 在 三氯氧磷 作用下， 反应 2.0h， 以86%的产率得到8-Amino-9-<β-D-(tetra-O-acetyl)glucopyranosyl>-1-methyl-2-(methylthio)purin-6(1H)-one
  参考文献：
  名称：

  A new one-step synthesis of 8-aminopurine nucleoside analogs from 6-(glycosylamino)-5-nitrosopyrimidines

  摘要：

  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.

  DOI：

  10.1021/jo00028a031
• 作为产物：
  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

• 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.
• Novel Procedure for Selective C-Nitrosation of Aminopyrimidine Derivatives Under Neutral Conditions. Scope and Synthetic Applications
  作者：Antonio Marchal、Manuel Melguizo、Manuel Nogueras、Adolfo Sánchez、John N. Low

  DOI：10.1055/s-2002-19760

  日期：——

  A novel simple method, based on treatment with isoamyl nitrite (IAN) in DMSO without any added acid, to produce selective C(5)-nitrosation of aminopyrimidine derivatives is described. It proved to be suitable for a multigram scale and applicable to a larger range of pyrimidine derivatives, including amino-dialkoxypyrimidines, than the procedures previously known. Its scope is analyzed and some example on the usefulness of the newly prepared substances as intermediates in the synthesis of fused heterobicyclic derivatives of potential biological interest is presented.

  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。