1'-deoxy-1'-(3-fluorophenyl)-β-D-ribofuranose | 304436-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-deoxy-1'-(3-fluorophenyl)-β-D-ribofuranose
• 英文别名: 1'-deoxy-1'-(3-fluorophenyl)-beta-D-ribofuranose；(2S,3R,4S,5R)-2-(3-fluorophenyl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 304436-63-3
• 化学式: C₁₁H₁₃FO₄
• 分子量: 228.22
• InChiKey: SKQWWJNVPFZHCO-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-deoxy-1'-(3-fluorophenyl)-β-D-ribofuranose 在 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 24.0h， 生成 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis of Fluorobenzene and Benzimidazole Nucleic-Acid Analogues and Their Influence on Stability of RNA Duplexes

  摘要：

  Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T-m differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene . fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ... H H-bond.

  DOI：

  10.1002/1522-2675(20000809)83:8<1791::aid-hlca1791>3.0.co;2-k
• 作为产物：
  描述：

  2,3,5-三苄氧基-D-核糖酸-1,4-内酯 在 palladium dihydroxide 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1'-deoxy-1'-(3-fluorophenyl)-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis of Fluorobenzene and Benzimidazole Nucleic-Acid Analogues and Their Influence on Stability of RNA Duplexes

  摘要：

  Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T-m differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene . fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ... H H-bond.

  DOI：

  10.1002/1522-2675(20000809)83:8<1791::aid-hlca1791>3.0.co;2-k

文献信息

• A Modular Approach to Aryl-<i>C</i>-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and <scp>d</scp>-/<scp>l</scp>-<i>C</i>-Nucleoside Stereoisomers
  作者：Jan Štambaský、Vojtěch Kapras、Martin Štefko、Ondřej Kysilka、Michal Hocek、Andrei V. Malkov、Pavel Kočovský

  DOI：10.1021/jo201110z

  日期：2011.10.7

  generated from (S)-5a, with the enantiopure allylic carbonates (R)-9a,b has been developed as the key step in a new approach to C-nucleoside analogues. The anomeric center was thus constructed via a stereocontrolled formation of the C–O rather than C–C bond with retention of configuration. The resulting bisallyl ethers 15a,b (≥90% de and >99% ee) were converted into C-ribosides 29a,b via the Ru-catalyzed

  （S）-5a生成的对映纯单保护的铜（I）对映体的铱（I）催化与对映纯烯丙基碳酸酯（R）-9a，b的烯丙基化反应已成为开发C的新方法的关键步骤-核苷类似物。因此，异头物中心是通过立体控制形成的C–O而非C–C键并保留构型而构建的。将所得的双烯丙基醚15a，b（de≥90％，ee≥99 ％）转化为C-核苷29a，b通过Ru催化的闭环复分解，然后由OsO 4或RuO 4催化的非对映选择性二羟基化和脱保护。起始片段5a和9a，b的绝对构型的变化允许所有四个α/β- d / l-组合的立体控制合成。
• Synthesis of Fluorobenzene and Benzimidazole Nucleic-Acid Analogues and Their Influence on Stability of RNA Duplexes
  作者：Jörg Parsch、Joachim W. Engels

  DOI：10.1002/1522-2675(20000809)83:8<1791::aid-hlca1791>3.0.co;2-k

  日期：2000.8.9

  Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T-m differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene . fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ... H H-bond.