2-[(2R,3S,4R,5R)-4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-N-[(1S)-1-[(2R,3R,4R,5R)-3-hydroxy-4-methoxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-methoxypropyl]acetamide | 1400908-61-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2-[(2R,3S,4R,5R)-4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-N-[(1S)-1-[(2R,3R,4R,5R)-3-hydroxy-4-methoxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-methoxypropyl]acetamide
• CAS: 1400908-61-3
• 化学式: C₂₆H₃₇N₅O₁₃
• 分子量: 627.605
• InChiKey: WNSKJGCVGWZUST-WSLPPKJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  235
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 1H-1,2,4-三唑 、 sodium tetrahydroborate 、 sodium periodate 、 高氯酸 、 lithium hydroxide monohydrate 、 三氟甲磺酸三甲基硅酯 、 五氟苯酚 、 硫酸 、 10% Pd(OH)₂ on C 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氘代氯仿 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， -5.0~70.0 ℃ 、138.0 kPa 条件下， 反应 38.75h， 生成 2-[(2R,3S,4R,5R)-4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-N-[(1S)-1-[(2R,3R,4R,5R)-3-hydroxy-4-methoxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-methoxypropyl]acetamide
  参考文献：
  名称：

  Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside

  摘要：

  A new oxyacetamide-modified dinucleoside with 5'-(S) chirality, a hydrophobic 5'-C-(2-methoxyethyl) group, and a 2'-O-methyl group was synthesized from D-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5' and 3' ends were found to be 'S'- and 'N'-types, respectively. These results were substantiated by ab initio density functional theory.

  DOI：

  10.1055/s-0031-1289783

文献信息

• Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside
  作者：Dilip Dhavale、Amit Jabgunde、Sachin Yeole、Shrihari Sanap、Shridhar Gadre

  DOI：10.1055/s-0031-1289783

  日期：2012.7

  A new oxyacetamide-modified dinucleoside with 5'-(S) chirality, a hydrophobic 5'-C-(2-methoxyethyl) group, and a 2'-O-methyl group was synthesized from D-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5' and 3' ends were found to be 'S'- and 'N'-types, respectively. These results were substantiated by ab initio density functional theory.