1-<2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl>thymine | 160053-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl>thymine
• 英文别名: 1-[2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl]thymine；1-[(3aR,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-4-phenyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-5-methylpyrimidine-2,4-dione
• CAS: 160053-60-1
• 化学式: C₁₉H₂₂N₂O₆
• 分子量: 374.393
• InChiKey: XWHMZFDATBPTEG-GPINWOSQSA-N

物化性质

• 密度：
  1.303±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 1-<2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl>thymine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 以21%的产率得到1-<2,3-O-isopropylidene-1-phenyl-5-O-(p-toluenesulfonyl)-α-D-ribofuranosyl>thymine
  参考文献：
  名称：

  A Ribonolactone-Based Approach to the Synthesis of 1′-Carbon-Substituted Thymine Ribonucleosides

  摘要：

  Thymine ribonucleosides bearing a carbon substituent at the anomeric position were synthesized starting from D-ribonolactone by way of nucleophilic addition reaction of organolithium reagents and subsequent condensation with trimethylsilylated thymine.

  DOI：

  10.1080/15257779408013242
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 35.83h， 生成 1-<2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl>thymine
  参考文献：
  名称：

  A Ribonolactone-Based Approach to the Synthesis of 1′-Carbon-Substituted Thymine Ribonucleosides

  摘要：

  Thymine ribonucleosides bearing a carbon substituent at the anomeric position were synthesized starting from D-ribonolactone by way of nucleophilic addition reaction of organolithium reagents and subsequent condensation with trimethylsilylated thymine.

  DOI：

  10.1080/15257779408013242

文献信息

• Synthesis of 1'-phenyl substituted nucleoside analogs
  作者：T NASR、Y TANIGUCHI、S SASAKI

  DOI：10.1016/s0385-5414(07)81201-9

  日期：2007.12.1

  1'-Phenyl substituted ribonucleoside analogs with all four nucleobases have been synthesized by the conventional N-glycosidation method.
• A Ribonolactone-Based Approach to the Synthesis of 1′-Carbon-Substituted Thymine Ribonucleosides
  作者：Hiroyuki Hayakawa、Michiko Miyazawa、Hiromichi Tanaka、Tadashi Miyasaka

  DOI：10.1080/15257779408013242

  日期：1994.3

  Thymine ribonucleosides bearing a carbon substituent at the anomeric position were synthesized starting from D-ribonolactone by way of nucleophilic addition reaction of organolithium reagents and subsequent condensation with trimethylsilylated thymine.