8-Amino-9-β-D-xylopyranosyl-2-(methylthio)purin-6(1H)-one | 137363-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Amino-9-β-D-xylopyranosyl-2-(methylthio)purin-6(1H)-one
• 英文别名: 8-amino-2-methylsulfanyl-9-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]-1H-purin-6-one
• CAS: 137363-10-1
• 化学式: C₁₁H₁₅N₅O₅S
• 分子量: 329.337
• InChiKey: GDRCBFJQUZIOSW-FTWQFJAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-Amino-9-<β-D-(tri-O-acetyl)xylopyranosyl>-2-(methylthio)purin-6(1H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以88%的产率得到8-Amino-9-β-D-xylopyranosyl-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

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.