1-<2-O-methoxalyl-2-C-(2-phenylethynyl)-3,5-O--β-D-arabino-pentofuranosyl>uracil | 175232-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<2-O-methoxalyl-2-C-(2-phenylethynyl)-3,5-O--β-D-arabino-pentofuranosyl>uracil
• 英文别名: 2-O-[(6aR,8R,9S,9aR)-8-(2,4-dioxopyrimidin-1-yl)-9-(2-phenylethynyl)-2,2,4,4-tetra(propan-2-yl)-6,6a,8,9a-tetrahydrofuro[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] 1-O-methyl oxalate
• CAS: 175232-26-5
• 化学式: C₃₂H₄₄N₂O₁₀Si₂
• 分子量: 672.88
• InChiKey: NRJKSITYQQKEBY-JPRUYBDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-<2-O-methoxalyl-2-C-(2-phenylethynyl)-3,5-O--β-D-arabino-pentofuranosyl>uracil 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 27.5h， 生成 (2'R)-2'-deoxy-2'-C-(2-phenethyl)-3',5'-O--uridine
  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：

  甲基戊酰氯 、 1-<2-C-(2-phenylethynyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>uracil 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到1-<2-O-methoxalyl-2-C-(2-phenylethynyl)-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

文献信息

• Nucleosides and Nucleotides. 139. Stereoselective Synthesis of (2′<i>S</i>)-2′-<i>C</i>-Alkyl-2′-deoxyuridines
  作者：Tomoharu Iino、Satoshi Shuto、Akira Matsuda

  DOI：10.1080/07328319608002378

  日期：1996.1

  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.