5'-O-(4,4'-Dimethoxytrityl)-8-(acetoxymethyl)-3,N4-etheno-2'-deoxycytidine | 264910-95-4

• 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)-8-(acetoxymethyl)-3,N4-etheno-2'-deoxycytidine
• 英文别名: 5'-O-(4,4'-Dimethoxytrityl)-8-(acetoxymethyl)-3,N⁴-etheno-2'-deoxycytidine
• CAS: 264910-95-4
• 化学式: C₃₅H₃₅N₃O₈
• 分子量: 625.678
• InChiKey: ZDTWOPJALGOVEI-RKKDRKJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122.75
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5'-O-(4,4'-Dimethoxytrityl)-8-(acetoxymethyl)-3,N4-etheno-2'-deoxycytidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到5'-O-(4,4'-Dimethoxytrityl)-3'-O-[2-cyanoethyl(N,N-diisopropyl)phosphinyl]-8-(acetoxymethyl)-3,N⁴-etheno-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 8-(Hydroxymethyl)-3,N⁴-etheno-2‘-deoxycytidine, a Potential Carcinogenic Glycidaldehyde Adduct, and Its Site-Specific Incorporation into DNA Oligonucleotides

  摘要：

  The previously unreported glycidaldehyde adduct, 8-(hydroxymethyl)-3,N-4-etheno-2'-deoxycytidine (8-HM-epsilon dC), has been synthesized for the first time by reaction of 2'-deoxycytidine with bromoacetaldehyde at pH 4.5, followed by reduction with sodium borohydride. The adduct was characterized by UV, MS, and NMR. The compound was stable to neutral and acidic conditions but not in alkaline solution. The corresponding phosphoramidite was synthesized in good yield from the intermediate, 3,N-4-ethenocarbaldehyde-2'-deoxycytidine using the standard methodology and site-specifically incorporated in both 15- and 25-mer oligonucleotides, for studies on biochemical and biophysical properties. The resulting oligonucleotides were purified using HPLC, and the base composition was verified by HPLC after enzymatic digestion.

  DOI：

  10.1021/tx990181m
• 作为产物：
  描述：

  5'-O-(4,4'-Dimethoxytrityl)-3,N4-ethenocarbaldehyde-2'-deoxycytidine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 73.0h， 生成 5'-O-(4,4'-Dimethoxytrityl)-8-(acetoxymethyl)-3,N4-etheno-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 8-(Hydroxymethyl)-3,N⁴-etheno-2‘-deoxycytidine, a Potential Carcinogenic Glycidaldehyde Adduct, and Its Site-Specific Incorporation into DNA Oligonucleotides

  摘要：

  The previously unreported glycidaldehyde adduct, 8-(hydroxymethyl)-3,N-4-etheno-2'-deoxycytidine (8-HM-epsilon dC), has been synthesized for the first time by reaction of 2'-deoxycytidine with bromoacetaldehyde at pH 4.5, followed by reduction with sodium borohydride. The adduct was characterized by UV, MS, and NMR. The compound was stable to neutral and acidic conditions but not in alkaline solution. The corresponding phosphoramidite was synthesized in good yield from the intermediate, 3,N-4-ethenocarbaldehyde-2'-deoxycytidine using the standard methodology and site-specifically incorporated in both 15- and 25-mer oligonucleotides, for studies on biochemical and biophysical properties. The resulting oligonucleotides were purified using HPLC, and the base composition was verified by HPLC after enzymatic digestion.

  DOI：

  10.1021/tx990181m