1-<2-C-(4-dimethylthexylsilyloxy-1-butynyl)-2-O-methoxalyl-3,5-O--β-D-arabino-pentofuranosyl>uracil | 175232-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<2-C-(4-dimethylthexylsilyloxy-1-butynyl)-2-O-methoxalyl-3,5-O--β-D-arabino-pentofuranosyl>uracil
• CAS: 175232-27-6
• 化学式: C₃₆H₆₂N₂O₁₁Si₃
• 分子量: 783.152
• InChiKey: NNEHVISMFWKXJS-AFULWMRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  153.61
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-<2-C-(4-dimethylthexylsilyloxy-1-butynyl)-2-O-methoxalyl-3,5-O--β-D-arabino-pentofuranosyl>uracil 在 palladium on activated charcoal 偶氮二异丁腈 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 作用下， 以 乙酸乙酯 为溶剂， 反应 26.17h， 生成 1-[(2R,4S,5R)-4-Hydroxy-3-(4-hydroxy-butyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleosides and Nucleotides. 139. Stereoselective Synthesis of (2′S)-2′-C-Alkyl-2′-deoxyuridines

  摘要：

  A synthetic method for (2'S)-2'-C-alkyl-2'-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2'S)-2'-alkyl-2'-deoxy-3',5'-O-TIPDS-uridines (7) along with a small amount of their 2'R epimers.

  DOI：

  10.1080/07328319608002378
• 作为产物：
  描述：

  4-dimethylthexylsilyloxy-1-butyne 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-<2-C-(4-dimethylthexylsilyloxy-1-butynyl)-2-O-methoxalyl-3,5-O--β-D-arabino-pentofuranosyl>uracil
  参考文献：
  名称：

  Nucleosides and Nucleotides. 139. Stereoselective Synthesis of (2′S)-2′-C-Alkyl-2′-deoxyuridines

  摘要：

  A synthetic method for (2'S)-2'-C-alkyl-2'-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-beta-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2'S)-2'-alkyl-2'-deoxy-3',5'-O-TIPDS-uridines (7) along with a small amount of their 2'R epimers.

  DOI：

  10.1080/07328319608002378