3-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene | 1445870-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene
• CAS: 1445870-28-9
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: RCHPMUGUKWGNIU-DSNGMDLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene 在 吡啶 、 Pd(OH)2/C, 20% 、 三乙胺 、 N,N-二异丙基乙胺 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-benzoyloxy-3-{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-methoxymethoxyphenyllithium 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 3-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene
  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