[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-methyl-2-morpholin-4-yl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate | 183668-53-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-methyl-2-morpholin-4-yl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 183668-53-3
• 化学式: C₂₀H₂₇N₃O₉
• 分子量: 453.449
• InChiKey: HSXSWLXJSCRTEU-YWTNHNAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-methyl-2-morpholin-4-yl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以69%的产率得到1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2-morpholin-4-yl-1H-pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of 5-methylisocytidine derivatives

  摘要：

  N-2-Substituted 5-methylisocytidine derivatives were synthesized from S-2-methyl-2-thiothymine either by direct substitution of the methylthio group by an amino group and subsequent condensation with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose to give the acetylated nucleoside or by the opposite sequence first preparing an acetylated S,S-2-dimethyl-2-thiouridine followed by treatment with the appropriate amine.

  DOI：

  10.1007/bf00810888
• 作为产物：
  描述：

  2-(甲基硫代)-5-甲基嘧啶-4(1H)-酮 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-methyl-2-morpholin-4-yl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of 5-methylisocytidine derivatives

  摘要：

  N-2-Substituted 5-methylisocytidine derivatives were synthesized from S-2-methyl-2-thiothymine either by direct substitution of the methylthio group by an amino group and subsequent condensation with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose to give the acetylated nucleoside or by the opposite sequence first preparing an acetylated S,S-2-dimethyl-2-thiouridine followed by treatment with the appropriate amine.

  DOI：

  10.1007/bf00810888