N²-Benzoyl-2'-deoxy-5'-O-(dimethoxytrityl)-3'-O-(5'-O-thymidyldiisopropylsilyl)cytidine

• 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: N²-Benzoyl-2'-deoxy-5'-O-(dimethoxytrityl)-3'-O-(5'-O-thymidyldiisopropylsilyl)cytidine
• 英文别名: N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-di(propan-2-yl)silyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• 化学式: C₅₃H₆₁N₅O₁₂Si
• 分子量: 988.179
• InChiKey: QEONJOAWHKCOSU-ZZFTTXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  71
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  196
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  [[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-di(propan-2-yl)silyl] trifluoromethanesulfonate 、 beta-胸苷 在 2,6-二叔丁基-4-甲基吡啶 作用下， 反应 1.0h， 以70%的产率得到N²-Benzoyl-2'-deoxy-5'-O-(dimethoxytrityl)-3'-O-(5'-O-thymidyldiisopropylsilyl)cytidine
  参考文献：
  名称：

  Diisopropylsilyl-linked oligonucleotide analogs: solid-phase synthesis and physicochemical properties

  摘要：

  A novel synthetic method has been developed for efficient preparation of silyl-linked oligodeoxyribonucleotide analogs. The method allows, for the first time, automated solid-phase synthesis of long oligomers uniformly linked with the silyl internucleoside bridge. Synthesis of a thymidylate decanucleotide analog (14) illustrates this advance. The preparation of chimeric oligodeoxyribonucleotides containing single or multiple diisopropylsilyl backbone structures along with natural phosphodiester links is also described. These mixed backbone DNA strands were soluble and chemically stable in buffered aqueous solutions, as required for physicochemical study. These oligomers demonstrated excellent stability toward cleavage by 3'-exonuclease and good binding affinity with complementary oligonucleotides.

  DOI：

  10.1021/jo00079a030

文献信息

• Diisopropylsilyl-linked oligonucleotide analogs: solid-phase synthesis and physicochemical properties
  作者：Ashis K. Saha、Mark Sardaro、Cheryl Waychunas、Daniel Delecki、L. I. Kruse、Rusty Kutny、Paul Cavanaugh、Anne Yawman、Donald A. Upson

  DOI：10.1021/jo00079a030

  日期：1993.12

  A novel synthetic method has been developed for efficient preparation of silyl-linked oligodeoxyribonucleotide analogs. The method allows, for the first time, automated solid-phase synthesis of long oligomers uniformly linked with the silyl internucleoside bridge. Synthesis of a thymidylate decanucleotide analog (14) illustrates this advance. The preparation of chimeric oligodeoxyribonucleotides containing single or multiple diisopropylsilyl backbone structures along with natural phosphodiester links is also described. These mixed backbone DNA strands were soluble and chemically stable in buffered aqueous solutions, as required for physicochemical study. These oligomers demonstrated excellent stability toward cleavage by 3'-exonuclease and good binding affinity with complementary oligonucleotides.