(5R,6R,8R,9S)-6-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-9-hydroxy-8-(hydroxymethyl)-7-oxa-1-azaspiro[4.4]nonan-2-one | 1616261-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,6R,8R,9S)-6-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-9-hydroxy-8-(hydroxymethyl)-7-oxa-1-azaspiro[4.4]nonan-2-one
• 英文别名: (5R,6R,8R,9S)-6-(4-amino-2-oxopyrimidin-1-yl)-9-hydroxy-8-(hydroxymethyl)-7-oxa-1-azaspiro[4.4]nonan-2-one
• CAS: 1616261-90-5
• 化学式: C₁₂H₁₆N₄O₅
• 分子量: 296.283
• InChiKey: PFHDUAYWIPNXSY-XYHAGOFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3',5'-O-(四异丙基二硅氧烷-1,3-二基)-2'-氧代尿苷 在 4-二甲氨基吡啶 、 sodium azide 、 15-冠醚-5 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氨 、 氢气 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.17h， 生成 (5R,6R,8R,9S)-6-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-9-hydroxy-8-(hydroxymethyl)-7-oxa-1-azaspiro[4.4]nonan-2-one
  参考文献：
  名称：

  Syntheses of nucleosides with 2′-spirolactam and 2′-spiropyrrolidine moieties as potential inhibitors of hepatitis C virus NS5B polymerase

  摘要：

  To discover novel nucleosides as potential antiviral agents, 2'-spirolactam and 2'-spiropyrrolidine-containing nucleoside analogs were envisioned. Efficient synthetic routes were developed with an epoxide opening as the key step to establish the quaternary center at the 2' position, leading to the design and synthesis of uridine analogs 8 and 21, prodrugs 13-16, and cytidine analog 11. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.051

文献信息

• Syntheses of nucleosides with 2′-spirolactam and 2′-spiropyrrolidine moieties as potential inhibitors of hepatitis C virus NS5B polymerase
  作者：Qun Dang、Zhibo Zhang、Bingyu Tang、Yang Song、Ling Wu、Tongqian Chen、Stephane Bogen、Vinay Girijavallabhan、David B. Olsen、Peter T. Meinke

  DOI：10.1016/j.tetlet.2014.05.051

  日期：2014.7

  To discover novel nucleosides as potential antiviral agents, 2'-spirolactam and 2'-spiropyrrolidine-containing nucleoside analogs were envisioned. Efficient synthetic routes were developed with an epoxide opening as the key step to establish the quaternary center at the 2' position, leading to the design and synthesis of uridine analogs 8 and 21, prodrugs 13-16, and cytidine analog 11. (C) 2014 Elsevier Ltd. All rights reserved.