5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-5-formyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite | 1311141-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-5-formyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• 英文别名: N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-5-formyl-2-oxopyrimidin-4-yl]acetamide
• CAS: 1311141-25-9
• 化学式: C₄₂H₅₀N₅O₉P
• 分子量: 799.861
• InChiKey: SXXIJMGJXPVKHC-FYJGSNHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5-碘-2'-脱氧胞苷 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 pyridine hydrofluoride 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、344.75 kPa 条件下， 反应 5.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-5-formyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
  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

文献信息

• Catalytic Space Engineering as a Strategy to Activate C–H Oxidation on 5-Methylcytosine in Mammalian Genome
  作者：Sushma Sappa、Debasis Dey、Babu Sudhamalla、Kabirul Islam

  DOI：10.1021/jacs.1c03815

  日期：2021.8.11
• Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA
  作者：Qing Dai、Chuan He

  DOI：10.1021/ol201189n

  日期：2011.7.1

  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.