1-(3,5-Cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine | 133634-76-1

• 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: 1-(3,5-Cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine
• 英文别名: 1-[(4aR,6R,7R,7aR)-7a-ethynyl-7-hydroxyspiro[4,4a,6,7-tetrahydrofuro[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 133634-76-1
• 化学式: C₁₈H₂₂N₂O₆
• 分子量: 362.382
• InChiKey: KPCDDDKBXDHINS-OSDKZWGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(3,5-Cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine 在 吡啶 作用下， 以90%的产率得到1-(2-O-Acetyl-3,5-cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 3′--ethynylnucleosides of thymine

  摘要：

  Reaction of 1-[2,5-di-O-(t-butyldimethylsilyl)-beta-D-erythro-pentofuranos-3-ulosyl]thymine with HC = CMgBr gives a (25:1) mixture of 3'-C-ethynyl nucleosides of thymine having beta-D-xylo and beta-D-ribo configuration. Reaction of 1-(2'-deoxy-5'-O-trityl-beta-D-glycero-pentofuran -3-ulosyl)thymine with HC = CMgBr gives the corresponding 3'-C-ethynyl-beta-D-threo-thymidine. The absolute configurations of the newly formed chiral centers at C-3' have been demonstrated by chemical means.

  DOI：

  10.1016/s0040-4020(01)96914-5
• 作为产物：
  描述：

  1-<2-O-(tert-Butyldimethylsilyl)-3-C-ethynyl-β-D-xylo-pentofuranosyl>thymine 在 吡啶 、 硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 1-(3,5-Cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 3′--ethynylnucleosides of thymine

  摘要：

  Reaction of 1-[2,5-di-O-(t-butyldimethylsilyl)-beta-D-erythro-pentofuranos-3-ulosyl]thymine with HC = CMgBr gives a (25:1) mixture of 3'-C-ethynyl nucleosides of thymine having beta-D-xylo and beta-D-ribo configuration. Reaction of 1-(2'-deoxy-5'-O-trityl-beta-D-glycero-pentofuran -3-ulosyl)thymine with HC = CMgBr gives the corresponding 3'-C-ethynyl-beta-D-threo-thymidine. The absolute configurations of the newly formed chiral centers at C-3' have been demonstrated by chemical means.

  DOI：

  10.1016/s0040-4020(01)96914-5