1-[(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl]-5-methyl-1H-pyrimidine-2,4-dione | 314297-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(1S,3R,4R,5S)-4-hydroxy-1-(hydroxymethyl)-6-(2,2,2-trifluoroacetyl)-2-oxa-6-azabicyclo[3.2.0]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 314297-06-8
• 化学式: C₁₃H₁₄F₃N₃O₆
• 分子量: 365.266
• InChiKey: BYBINBQVFFXTGN-MCOZSMFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 氨 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以87%的产率得到1-((1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6
• 作为产物：
  描述：

  5-甲基-1,3-二(三甲基硅烷基)-2,4(1H,3H)-嘧啶二酮 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 1-[(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6

文献信息

• Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer
  作者：Satoshi Obika、Jyun-ichi Andoh、Mayumi Onoda、Osamu Nakagawa、Akiko Hiroto、Tomomi Sugimoto、Takeshi Imanishi

  DOI：10.1016/s0040-4039(03)01279-6

  日期：2003.7

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.