((2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-2-yl)-methanol | 190506-34-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: ((2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-2-yl)-methanol
• 英文别名: [(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[2-fluoro-6-[2-(4-nitrophenyl)ethoxy]purin-9-yl]oxolan-2-yl]methanol
• CAS: 190506-34-4
• 化学式: C₂₄H₃₂FN₅O₆Si
• 分子量: 533.632
• InChiKey: SBDANRRAMMRPQW-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-2-yl)-methanol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 triethylamine trihydrofluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2-fluoroinosine
  参考文献：
  名称：

  A High-Yield Synthesis of Deoxy-2-Fluoroinosine and its Incorporation into Oligonucleotides.

  摘要：

  An improved synthesis of the deoxy-2-fluoroinosine nucleoside is described, that makes use of mild fluorination (polyvinylpyridinium polyhydrogenfluoride) and O-silyl deprotection (triethylamine trihydrofluoride) reactions. The derived 5'-dimethoxytrityl-2-fluoroinosine-3'-phosphoramidite was incorporated into 10-, 15- and 20- mer oligonucleotides containing up to 7 non-natural bases. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00540-6
• 作为产物：
  描述：

  3'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine 在 亚硝酸特丁酯 、 polyvinylpyridinium polyhydrogenfluoride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以70%的产率得到3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine
  参考文献：
  名称：

  A High-Yield Synthesis of Deoxy-2-Fluoroinosine and its Incorporation into Oligonucleotides.

  摘要：

  An improved synthesis of the deoxy-2-fluoroinosine nucleoside is described, that makes use of mild fluorination (polyvinylpyridinium polyhydrogenfluoride) and O-silyl deprotection (triethylamine trihydrofluoride) reactions. The derived 5'-dimethoxytrityl-2-fluoroinosine-3'-phosphoramidite was incorporated into 10-, 15- and 20- mer oligonucleotides containing up to 7 non-natural bases. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00540-6

文献信息

• A High-Yield Synthesis of Deoxy-2-Fluoroinosine and its Incorporation into Oligonucleotides.
  作者：Abdennaji Adib、Pierre F. Potier、Svetlana Doronina、Ivan Huc、Jean-Paul Behr

  DOI：10.1016/s0040-4039(97)00540-6

  日期：1997.4

  An improved synthesis of the deoxy-2-fluoroinosine nucleoside is described, that makes use of mild fluorination (polyvinylpyridinium polyhydrogenfluoride) and O-silyl deprotection (triethylamine trihydrofluoride) reactions. The derived 5'-dimethoxytrityl-2-fluoroinosine-3'-phosphoramidite was incorporated into 10-, 15- and 20- mer oligonucleotides containing up to 7 non-natural bases. (C) 1997 Published by Elsevier Science Ltd.