3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxycytidine | 1311141-17-9

• 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: 3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxycytidine
• 英文别名: 1-[(4aR,6R,7aS)-2,2-ditert-butyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-4-amino-5-iodopyrimidin-2-one
• CAS: 1311141-17-9
• 化学式: C₁₇H₂₈IN₃O₄Si
• 分子量: 493.417
• InChiKey: XGXVVQJSVNOOCC-YNEHKIRRSA-N

物化性质

• 沸点：
  491.5±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxycytidine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、344.75 kPa 条件下， 反应 3.0h， 生成 3',5'-O-di-t-butylsilyl-N4-acetyl-5-formyl-2'-deoxycytidine
  参考文献：
  名称：

  Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA

  摘要：

  To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.

  DOI：

  10.1021/ol201189n
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 、 5-碘-2'-脱氧胞苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以95%的产率得到3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxycytidine
  参考文献：
  名称：

  Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA

  摘要：

  To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.

  DOI：

  10.1021/ol201189n