5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine | 157770-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine
• 英文别名: 1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoxolan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 157770-11-1
• 化学式: C₃₆H₄₃FN₂O₈Si
• 分子量: 678.83
• InChiKey: ATNFXPDTMCWXTB-WTGZKXAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine 2'-(cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(Cyanoethyl N,N-diisopropylphosphoramidite) and Its Use in the Synthesis of RNA

  摘要：

  5-Fluorouridine (FUrd) has been successfully converted to 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(cyanoethyl N,N-diisopropyl(phosphoramidite) by methods similar to those employed for the preparation of other ribonucleoside phosphoramidites. The desired product, as well as its precursors and the incorrect regioisomers, are prepared and fully characterized by H-1 NMR, F-19 NMR, P-31 NMR, FAR-MS, UV absorbance, elemental analysis, and melting points. The purified material is used for the production of RNA by solid-phase methods. Coupling yields of 94% are obtained with this material. The resulting RNA is readily purified and used for biophysical studies. The self-complemetary RNA decamer 5'-rGCGAAU(FU)CGC is prepared and purified. The material adopts an A-form duplex in solution at neutral pH as characterized by CD spectroscopy. The thermal stability of the duplex is similar to the parent duplex oligoribonucleotide prepared with uridine instead of 5-fluorouridine. The control duplex has a T-m of 53.8 and the FUrd substituted duplex has a T-m of 56.6 (xb0)degrees C as determined by UV hyperchromicity at 260 nm. The CD spectra and UV hyperchromicity data for the duplex oligoribonucleotide containing FUrd have a slight pH dependence indicating that ionization of FUrd has a slight but measurable impact on RNA duplex stability. 1D NMR spectroscopy of the imino hydrogens for this duplex in H2O solution confirms the formation of Watson-Crick base pairs. The imino hydrogen resonance for the FUrd-A base pair is moved downfield and broadened compared with a control duplex oligoribonucleotide as a consequence of the electron-withdrawing inductive effect of fluorine.

  DOI：

  10.1021/jo00098a044
• 作为产物：
  描述：

  5-氟尿嘧啶核苷 在 吡啶 、 咪唑 作用下， 反应 5.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine
  参考文献：
  名称：

  Synthesis of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(Cyanoethyl N,N-diisopropylphosphoramidite) and Its Use in the Synthesis of RNA

  摘要：

  5-Fluorouridine (FUrd) has been successfully converted to 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(cyanoethyl N,N-diisopropyl(phosphoramidite) by methods similar to those employed for the preparation of other ribonucleoside phosphoramidites. The desired product, as well as its precursors and the incorrect regioisomers, are prepared and fully characterized by H-1 NMR, F-19 NMR, P-31 NMR, FAR-MS, UV absorbance, elemental analysis, and melting points. The purified material is used for the production of RNA by solid-phase methods. Coupling yields of 94% are obtained with this material. The resulting RNA is readily purified and used for biophysical studies. The self-complemetary RNA decamer 5'-rGCGAAU(FU)CGC is prepared and purified. The material adopts an A-form duplex in solution at neutral pH as characterized by CD spectroscopy. The thermal stability of the duplex is similar to the parent duplex oligoribonucleotide prepared with uridine instead of 5-fluorouridine. The control duplex has a T-m of 53.8 and the FUrd substituted duplex has a T-m of 56.6 (xb0)degrees C as determined by UV hyperchromicity at 260 nm. The CD spectra and UV hyperchromicity data for the duplex oligoribonucleotide containing FUrd have a slight pH dependence indicating that ionization of FUrd has a slight but measurable impact on RNA duplex stability. 1D NMR spectroscopy of the imino hydrogens for this duplex in H2O solution confirms the formation of Watson-Crick base pairs. The imino hydrogen resonance for the FUrd-A base pair is moved downfield and broadened compared with a control duplex oligoribonucleotide as a consequence of the electron-withdrawing inductive effect of fluorine.

  DOI：

  10.1021/jo00098a044

文献信息

• Synthesis of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(Cyanoethyl N,N-diisopropylphosphoramidite) and Its Use in the Synthesis of RNA
  作者：William H. Gmeiner、Parag Sahasrabudhe、Richard T. Pon

  DOI：10.1021/jo00098a044

  日期：1994.9

  5-Fluorouridine (FUrd) has been successfully converted to 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(cyanoethyl N,N-diisopropyl(phosphoramidite) by methods similar to those employed for the preparation of other ribonucleoside phosphoramidites. The desired product, as well as its precursors and the incorrect regioisomers, are prepared and fully characterized by H-1 NMR, F-19 NMR, P-31 NMR, FAR-MS, UV absorbance, elemental analysis, and melting points. The purified material is used for the production of RNA by solid-phase methods. Coupling yields of 94% are obtained with this material. The resulting RNA is readily purified and used for biophysical studies. The self-complemetary RNA decamer 5'-rGCGAAU(FU)CGC is prepared and purified. The material adopts an A-form duplex in solution at neutral pH as characterized by CD spectroscopy. The thermal stability of the duplex is similar to the parent duplex oligoribonucleotide prepared with uridine instead of 5-fluorouridine. The control duplex has a T-m of 53.8 and the FUrd substituted duplex has a T-m of 56.6 (xb0)degrees C as determined by UV hyperchromicity at 260 nm. The CD spectra and UV hyperchromicity data for the duplex oligoribonucleotide containing FUrd have a slight pH dependence indicating that ionization of FUrd has a slight but measurable impact on RNA duplex stability. 1D NMR spectroscopy of the imino hydrogens for this duplex in H2O solution confirms the formation of Watson-Crick base pairs. The imino hydrogen resonance for the FUrd-A base pair is moved downfield and broadened compared with a control duplex oligoribonucleotide as a consequence of the electron-withdrawing inductive effect of fluorine.