Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-cyano-6-oxo-4-phenyl-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester | 191659-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-cyano-6-oxo-4-phenyl-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[5-cyano-6-oxo-4-phenyl-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpyrimidin-1-yl]oxan-2-yl]methyl acetate
• CAS: 191659-48-0
• 化学式: C₃₉H₄₃N₃O₁₉S
• 分子量: 889.845
• InChiKey: DGVSWGNTJTVYIA-GARSWUAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  311
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-cyano-6-oxo-4-phenyl-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以81%的产率得到2,4-Dioxo-6-phenyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Glycosylation of 2-Thiouracil Derivatives. A Synthetic Approach to 3-Glycosyl-2, 4-dioxypyrimidines

  摘要：

  Reaction of 6-aryl-5-cyano-2-thiouracils 2a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. However, their deacetylation with ammonia in methanol caused a cleavage of the S-glycosyl residue and gave the N-3 glycosylated analogues 6a-h.

  DOI：

  10.1080/07328319708001360
• 作为产物：
  描述：

  Potassium; 5-cyano-4-oxo-6-phenyl-1,4-dihydro-pyrimidine-2-thiolate 在 氢氧化钾 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-cyano-6-oxo-4-phenyl-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6H-pyrimidin-1-yl]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Glycosylation of 2-Thiouracil Derivatives. A Synthetic Approach to 3-Glycosyl-2, 4-dioxypyrimidines

  摘要：

  Reaction of 6-aryl-5-cyano-2-thiouracils 2a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. However, their deacetylation with ammonia in methanol caused a cleavage of the S-glycosyl residue and gave the N-3 glycosylated analogues 6a-h.

  DOI：

  10.1080/07328319708001360