3',5'-O-bis(tert-butyldimethylsilyl)-5-cyanomethyl-2'-deoxycytidine | 923261-30-7

• 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: 3',5'-O-bis(tert-butyldimethylsilyl)-5-cyanomethyl-2'-deoxycytidine
• 英文别名: 2-[4-amino-1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-oxopyrimidin-5-yl]acetonitrile
• CAS: 923261-30-7
• 化学式: C₂₃H₄₂N₄O₄Si₂
• 分子量: 494.782
• InChiKey: ZVDIGZCSUPMFPX-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',5'-O-bis(tert-butyldimethylsilyl)-5-cyanomethyl-2'-deoxycytidine 在 氢气 、 镍 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以37%的产率得到3',5'-O-bis(tert-butyldimethylsilyl)-5-(2-aminoethyl)-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis and Fluorescent Properties of Bi- and Tricyclic 4-N-Carbamoyldeoxycytidine Derivatives

  摘要：

  [GRAPHICS]New bi- and tricyclic deoxycytidine derivatives (dC(hpd), dC(mpp), dC(tpp), dC(ppp)) were synthesized as analogues of a fluorescent nucleoside, dC(hpp), previously reported. The carbamoyl group of dC(hpd) and the 5-position of the cytosine ring are bridged via an ethylene linker so that the modified group forms a nonplanar structure with the cytosine ring. The fluorescent study of dC(hpd) indicated that the coplanar structure between the carbamoyl group and the cytosine ring is of importance. N-Methylation of the carbamoyl group (dC(mpp)) weakened the intensity of the fluorescence of dC(hpp), and the derivative (dC(tpp)), which had a thiocarbamoyl group, lost its fluorescent property. Moreover, addition of a pyrrolo-ring (dC(ppp)) to dC(hpp) enhanced the intensity of fluorescence, and an emission light was observed with a marked Stokes shift of 120 nm.

  DOI：

  10.1021/jo0617767
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 1H-1,2,4-三唑 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 、 三氯氧磷 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 3',5'-O-bis(tert-butyldimethylsilyl)-5-cyanomethyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis and Fluorescent Properties of Bi- and Tricyclic 4-N-Carbamoyldeoxycytidine Derivatives

  摘要：

  [GRAPHICS]New bi- and tricyclic deoxycytidine derivatives (dC(hpd), dC(mpp), dC(tpp), dC(ppp)) were synthesized as analogues of a fluorescent nucleoside, dC(hpp), previously reported. The carbamoyl group of dC(hpd) and the 5-position of the cytosine ring are bridged via an ethylene linker so that the modified group forms a nonplanar structure with the cytosine ring. The fluorescent study of dC(hpd) indicated that the coplanar structure between the carbamoyl group and the cytosine ring is of importance. N-Methylation of the carbamoyl group (dC(mpp)) weakened the intensity of the fluorescence of dC(hpp), and the derivative (dC(tpp)), which had a thiocarbamoyl group, lost its fluorescent property. Moreover, addition of a pyrrolo-ring (dC(ppp)) to dC(hpp) enhanced the intensity of fluorescence, and an emission light was observed with a marked Stokes shift of 120 nm.

  DOI：

  10.1021/jo0617767