N3-benzoyl-2'-O-trimethylsilyl-3',5'-O-(di-tert-butylsilanediyl)uridine | 1330027-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N3-benzoyl-2'-O-trimethylsilyl-3',5'-O-(di-tert-butylsilanediyl)uridine
• 英文别名: 1-[(4aR,6R,7R,7aR)-2,2-ditert-butyl-7-trimethylsilyloxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-3-benzoylpyrimidine-2,4-dione
• CAS: 1330027-09-2
• 化学式: C₂₇H₄₀N₂O₇Si₂
• 分子量: 560.795
• InChiKey: CQOKKVBIOPBUDA-VDEHWKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-芘甲醛 、 N3-benzoyl-2'-O-trimethylsilyl-3',5'-O-(di-tert-butylsilanediyl)uridine 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.08h， 以53%的产率得到N3-benzoyl-2'-O-(1-pyrenylmethyl)-3',5'-O-(di-tert-butylsilanediyl)uridine
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate-promoted Reductive 2′-O-arylmethylation of Ribonucleoside Derivatives

  摘要：

  Arylmethyl groups such as benzyl, p-methoxybenzyl, and 1-pyrenylmethyl groups were introduced to the 2'-O-position of nucleosides by reductive etherification. Combining corresponding aromatic aldehydes with 2'-O-trimethylsilylnucleoside derivatives in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) resulted in moderate to good yields of the 2'-O-arylmethyluridine derivatives, whereas the corresponding cytidine and adenosine derivatives were obtained in low yields. The reaction of ribonucleosides with aliphatic aldehydes did not proceed smoothly. Anomerization of the uridine derivatives by TMSOTf was observed in CH(2)Cl(2), toluene, and CH(3)CN, but was completely suppressed when the reactions were conducted in 1,4-dioxane.

  DOI：

  10.1080/15257770.2011.592171
• 作为产物：
  描述：

  三甲基氯硅烷 、 二叔丁基硅基双(三氟甲烷磺酸) 、 苯甲酰氯 、 尿嘧啶核苷 在 咪唑 、 吡啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.34h， 以96%的产率得到N3-benzoyl-2'-O-trimethylsilyl-3',5'-O-(di-tert-butylsilanediyl)uridine
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate-promoted Reductive 2′-O-arylmethylation of Ribonucleoside Derivatives

  摘要：

  Arylmethyl groups such as benzyl, p-methoxybenzyl, and 1-pyrenylmethyl groups were introduced to the 2'-O-position of nucleosides by reductive etherification. Combining corresponding aromatic aldehydes with 2'-O-trimethylsilylnucleoside derivatives in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) resulted in moderate to good yields of the 2'-O-arylmethyluridine derivatives, whereas the corresponding cytidine and adenosine derivatives were obtained in low yields. The reaction of ribonucleosides with aliphatic aldehydes did not proceed smoothly. Anomerization of the uridine derivatives by TMSOTf was observed in CH(2)Cl(2), toluene, and CH(3)CN, but was completely suppressed when the reactions were conducted in 1,4-dioxane.

  DOI：

  10.1080/15257770.2011.592171