2‘-desoxy-2‘[4-(2-furyl)butanamido]-5’O-(4,4‘-dimethoxytrityl)uridine | 1577186-77-6

• 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: 2‘-desoxy-2‘[4-(2-furyl)butanamido]-5’O-(4,4‘-dimethoxytrityl)uridine
• CAS: 1577186-77-6
• 化学式: C₃₈H₃₉N₃O₉
• 分子量: 681.742
• InChiKey: CVMWECNMEIEARW-MBWVZDRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  154.25
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl-N,N-diisopropylchlorophosphoramidite 、 2‘-desoxy-2‘[4-(2-furyl)butanamido]-5’O-(4,4‘-dimethoxytrityl)uridine 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以77%的产率得到2‘-desoxy-2‘-[(4-(2-furyle)butanamido)]-5‘-O-(4,4‘-dimethoxytrityl)-uridine-3’-(2-cyanoethyl)-N,N-diisopropyle phosphoramidite
  参考文献：
  名称：

  Synthesis of DNA Conjugates with Metalated Tetracationic Porphyrins by Postsynthetic Cycloadditions

  摘要：

  Tetracationic porphyrins of the TMPP (meso-tetra-(4-N-methylpyridyl)porphyrin) type, metalated with Cu(II) or with Au(III), were conjugated covalently to oligonucleotides. The Cu(I)-catalyzed cycloaddition (between an azide and an ethynyl group) and the Diels-Alder cycloaddition (between a furan and a maleimide functionality) were successfully applied as two alternative postsynthetic methods to modify the 2'-position of an internal uridine. Melting temperatures and UV/vis absorption properties were compared. CD measurements indicated that the type of conjugation chemistry determines the grade of intercalation of the attached and positively charged porphyrins.

  DOI：

  10.1021/ol500364j
• 作为产物：
  描述：

  furnish 2-(3-bromopropyl)furan 在 吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 102.5h， 生成 2‘-desoxy-2‘[4-(2-furyl)butanamido]-5’O-(4,4‘-dimethoxytrityl)uridine
  参考文献：
  名称：

  Synthesis of DNA Conjugates with Metalated Tetracationic Porphyrins by Postsynthetic Cycloadditions

  摘要：

  Tetracationic porphyrins of the TMPP (meso-tetra-(4-N-methylpyridyl)porphyrin) type, metalated with Cu(II) or with Au(III), were conjugated covalently to oligonucleotides. The Cu(I)-catalyzed cycloaddition (between an azide and an ethynyl group) and the Diels-Alder cycloaddition (between a furan and a maleimide functionality) were successfully applied as two alternative postsynthetic methods to modify the 2'-position of an internal uridine. Melting temperatures and UV/vis absorption properties were compared. CD measurements indicated that the type of conjugation chemistry determines the grade of intercalation of the attached and positively charged porphyrins.

  DOI：

  10.1021/ol500364j