1-allyloxy-4-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene | 1445870-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyloxy-4-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene
• CAS: 1445870-39-2
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: BCMYQJDCRUDQNR-GUQXXGRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-allyloxy-4-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene 在 吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 Pd(OH)2/C, 20% 、 三乙胺 、 N,N-二异丙基乙胺 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 21.92h， 生成 1-benzoyloxy-4-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene
  参考文献：
  名称：

  Base-pair recognition ability of hydroxyphenyl nucleobases in parallel triplex DNA

  摘要：

  Oligonucleotides containing 2'-deoxyribonucleotides bearing hydroxyphenyl nucleobases or their 2',4'-BNA-modified analogs were synthesized, and the triplex-forming ability of their oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. Results showed that 2'-deoxyribonucleotide bearing 2'-hydroxyphenyl nucleobase could be recognized by a dUA base pair while no affinity to a TA base pair was observed. The,4'-BNA modification led to a further increase in the binding affinity to a dUA base pair. The,4'-BNA bearing 3-hydroxyphenyl nucleobase showed moderate binding affinity to a TA base pair, but without selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.107
• 作为产物：
  描述：

  3,5-di-O-benzyl-2-deoxy-D-ribofuranose 、 4-allyloxyphenyllithium 在 三丁基膦 、 偶氮二甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以48%的产率得到1-allyloxy-4-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene
  参考文献：
  名称：

  Base-pair recognition ability of hydroxyphenyl nucleobases in parallel triplex DNA

  摘要：

  Oligonucleotides containing 2'-deoxyribonucleotides bearing hydroxyphenyl nucleobases or their 2',4'-BNA-modified analogs were synthesized, and the triplex-forming ability of their oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. Results showed that 2'-deoxyribonucleotide bearing 2'-hydroxyphenyl nucleobase could be recognized by a dUA base pair while no affinity to a TA base pair was observed. The,4'-BNA modification led to a further increase in the binding affinity to a dUA base pair. The,4'-BNA bearing 3-hydroxyphenyl nucleobase showed moderate binding affinity to a TA base pair, but without selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.107