5'-O-acetyl-α-thymidine | 158813-99-1

• 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: 5'-O-acetyl-α-thymidine
• CAS: 158813-99-1
• 化学式: C₁₂H₁₆N₂O₆
• 分子量: 284.269
• InChiKey: ACYSKFODOKGJMA-AEJSXWLSSA-N

物化性质

• 密度：
  1.381±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5'-O-acetyl-α-thymidine 在 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 27.0h， 生成 Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Targeting Chimeric alpha,beta-Oligonucleotides to the Flanks of a Stem in DNA. The Enhanced Effect of an Intercalator.

  摘要：

  3'-O-(4,4'-Dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (7) was prepared from alpha-thymidine by the reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 5. 3'-O-(4,4'-Dimethoxytrityl-alpha-thymidine (9) was synthesized by successive, 5'-O-acetylation, 3'-O-tritylation and 5'-O-deacetylation of alpha-thymidine. Phosphitylation of the 5'-hydroxy group of 7 and 9 afforded the amidites 8 and 10. These amidites and commercial beta-2'-deoxyribonucleoside-3'-phosphoramidites were used in the synthesis of chimeric ODNs with 3'-3' and 5'-5' internucleotidic phosphodiester linkages. The stability of a DNA three way junction (TWJ) was studied by observing the thermal melting when a DNA was targeted to the flanks of a hairpin. The TWJ was considerably stabilized when 7 and 9 were inserted into the junction region. The corresponding duplex obtained by deleting the hairpin, however, was destabilized on insertion of 7 and 9.

  DOI：

  10.3891/acta.chem.scand.51-1245
• 作为产物：
  描述：

  乙酸酐 、 Alpha-胸苷 以 吡啶 为溶剂， 以53%的产率得到5'-O-acetyl-α-thymidine
  参考文献：
  名称：

  Targeting Chimeric alpha,beta-Oligonucleotides to the Flanks of a Stem in DNA. The Enhanced Effect of an Intercalator.

  摘要：

  3'-O-(4,4'-Dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (7) was prepared from alpha-thymidine by the reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 5. 3'-O-(4,4'-Dimethoxytrityl-alpha-thymidine (9) was synthesized by successive, 5'-O-acetylation, 3'-O-tritylation and 5'-O-deacetylation of alpha-thymidine. Phosphitylation of the 5'-hydroxy group of 7 and 9 afforded the amidites 8 and 10. These amidites and commercial beta-2'-deoxyribonucleoside-3'-phosphoramidites were used in the synthesis of chimeric ODNs with 3'-3' and 5'-5' internucleotidic phosphodiester linkages. The stability of a DNA three way junction (TWJ) was studied by observing the thermal melting when a DNA was targeted to the flanks of a hairpin. The TWJ was considerably stabilized when 7 and 9 were inserted into the junction region. The corresponding duplex obtained by deleting the hairpin, however, was destabilized on insertion of 7 and 9.

  DOI：

  10.3891/acta.chem.scand.51-1245