(2R,4aR,6R,7S,8S,8aS)-7-hydroxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-8-carbonitrile | 923569-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6R,7S,8S,8aS)-7-hydroxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-8-carbonitrile
• CAS: 923569-29-3
• 化学式: C₁₉H₁₉N₃O₆
• 分子量: 385.376
• InChiKey: XLSNQFRVERSWBB-IJAXMKKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6R,7S,8S,8aS)-7-hydroxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-8-carbonitrile 在 吡啶 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.33h， 生成 1-(2,4,6-tri-O-acetyl-3-cyano-β-D-altropyranosyl) thymine
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 sodium hydroxide 、 sodium methylate 、 四氯化锡 、 对甲苯磺酸 、 异丙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 (2R,4aR,6R,7S,8S,8aS)-7-hydroxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-8-carbonitrile
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025