5'-O-[4,4'-dimethoxy-4''-(1H,1H,2H,2H-perfluorodecyl)trityl]-N²-isobutyryl-2'-deoxyguanosine | 865758-42-5

• 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'-dimethoxy-4''-(1H,1H,2H,2H-perfluorodecyl)trityl]-N²-isobutyryl-2'-deoxyguanosine
• 英文别名: N-[9-[(2R,4S,5R)-5-[[[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]-bis(4-methoxyphenyl)methoxy]methyl]-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 865758-42-5
• 化学式: C₄₅H₄₀F₁₇N₅O₇
• 分子量: 1085.81
• InChiKey: ILCRGXNZPONSRB-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  74
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  5'-O-[4,4'-dimethoxy-4''-(1H,1H,2H,2H-perfluorodecyl)trityl]-N²-isobutyryl-2'-deoxyguanosine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到2-Cyanoethyl ((2R,3S,5R)-2-(((4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl)bis(4-methoxyphenyl)methoxy)methyl)-5-(2-isobutyramido-6-oxo-3,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl) diisopropylphosphoramidite
  参考文献：
  名称：

  Fluorous Affinity Purification of Oligonucleotides

  摘要：

  Nucleoside phosphoramidites bearing a fluorous dimethoxytrityl (FDMT) group were used to synthesize fluorous-tagged oligonucleotides, which were subjected to solid-phase extraction using a pH-stable fluorinated adsorbent. On-column detritylation afforded the purified oligonucleotides. The fluorous affinity purification method offers one-pass loading without ammonia removal, high selectivity for the removal of failure sequences, high recoveries (typically 70-100%), and the ability to purify long oligonucleotides (e.g., 50-100-mers).

  DOI：

  10.1021/jo050795y
• 作为产物：
  描述：

  methyl 4-(1H,1H,2H,2H-perfluorodecyl)benzoate 在 吡啶 、 乙酰氯 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 20.0h， 生成 5'-O-[4,4'-dimethoxy-4''-(1H,1H,2H,2H-perfluorodecyl)trityl]-N²-isobutyryl-2'-deoxyguanosine
  参考文献：
  名称：

  Fluorous Affinity Purification of Oligonucleotides

  摘要：

  Nucleoside phosphoramidites bearing a fluorous dimethoxytrityl (FDMT) group were used to synthesize fluorous-tagged oligonucleotides, which were subjected to solid-phase extraction using a pH-stable fluorinated adsorbent. On-column detritylation afforded the purified oligonucleotides. The fluorous affinity purification method offers one-pass loading without ammonia removal, high selectivity for the removal of failure sequences, high recoveries (typically 70-100%), and the ability to purify long oligonucleotides (e.g., 50-100-mers).

  DOI：

  10.1021/jo050795y

文献信息

• Fluorous Affinity Purification of Oligonucleotides
  作者：William H. Pearson、David A. Berry、Patrick Stoy、Kee-Yong Jung、Anthony D. Sercel

  DOI：10.1021/jo050795y

  日期：2005.9.1

  Nucleoside phosphoramidites bearing a fluorous dimethoxytrityl (FDMT) group were used to synthesize fluorous-tagged oligonucleotides, which were subjected to solid-phase extraction using a pH-stable fluorinated adsorbent. On-column detritylation afforded the purified oligonucleotides. The fluorous affinity purification method offers one-pass loading without ammonia removal, high selectivity for the removal of failure sequences, high recoveries (typically 70-100%), and the ability to purify long oligonucleotides (e.g., 50-100-mers).