8-(N-methyl)amino-1,6-dihydro-1-methyl-2-methoxy-6-oxo-9-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)purine | 124516-19-4

• 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: 8-(N-methyl)amino-1,6-dihydro-1-methyl-2-methoxy-6-oxo-9-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)purine
• 英文别名: 8-Amino-9-<β-D-(tetra-O-acetyl)glucopyranosyl>-1-methyl-2-methoxypurin-6(1H)-one；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(8-amino-2-methoxy-1-methyl-6-oxopurin-9-yl)oxan-2-yl]methyl acetate
• CAS: 124516-19-4
• 化学式: C₂₁H₂₇N₅O₁₁
• 分子量: 525.472
• InChiKey: CQSYYSJVRYTCKU-IIRRGFMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  200
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  8-(N-methyl)amino-1,6-dihydro-1-methyl-2-methoxy-6-oxo-9-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)purine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以42%的产率得到1,6-Dihydro-8-amino-9-β-D-glucopyranosyl-1-methyl-2-methoxypurin-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：

  6-<<β-D-(Tetra-O-acetyl)glucopyranosyl>amino>-3-methyl-2-methoxy-5-nitrosopyrimidin-4(3H)-one 、 甲酰胺 生成 8-(N-methyl)amino-1,6-dihydro-1-methyl-2-methoxy-6-oxo-9-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamino)purine
  参考文献：
  名称：

  MELGUIZO, M.;NOGUERAS, M.;SANCHEZ, A.;QUIJANO, L., TETRAHEDRON LETT., 30,(1989) N0, C. 2669-2672

  摘要：

  DOI：

文献信息

• 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