1-benzoyloxy-2-(3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)benzene | 402859-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 1-benzoyloxy-2-(3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)benzene
• 英文别名: 1-benzoyloxy-2-(3,5-O-dibenzyl-2-O,4-C-methylene-β-D-ribofuranosyl)benzene；[2-[(1S,3S,4S,7S)-7-phenylmethoxy-1-(phenylmethoxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]phenyl] benzoate
• CAS: 402859-69-2
• 化学式: C₃₃H₃₀O₆
• 分子量: 522.598
• InChiKey: YKGBHBWUVFFHIW-QUUJSONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-benzoyloxy-2-(3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)benzene 在 Pd(OH)2/C, 20% 、 环己烯 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以89%的产率得到1-benzoyloxy-2-(2-O,4-C-methylene-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：

  (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 1-benzoyloxy-2-(3,5-di-O-benzyl-2-O,4-C-methylene-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

文献信息

• NOVEL NUCLEOSIDE ANALOGS AND OLIGONUCLEOTIDE DERIVATIVES CONTAINING THESE ANALOGS
  申请人：Imanishi, Takeshi

  公开号：EP1314734A1

  公开（公告）日：2003-05-28

  Nucleoside analogues expressed by the following general formula    where B represents an aromatic base having carbonyl oxygen at the 2-position, or a 2-hydroxyphenyl group, or oligonucleotide derivatives containing one or more of the nucleoside analogues are provided. The oligonucleotide derivatives are triplex-forming oligonucleotide derivatives which bind specifically to target double-stranded DNA with high affinity in the antigene method to form triplexes, and can thereby control and inhibit the expression of relevant genes efficiently, and which show high resistance to nucleases.

  提供了以下通式表达的核苷酸类似物：其中B代表具有2位羰基氧或2-羟基苯基基团的芳香碱基，或者含有一个或多个核苷酸类似物的寡核苷酸衍生物。这些寡核苷酸衍生物是三链体形成寡核苷酸衍生物，能够在抗原法中与目标双链DNA特异性结合，形成三链体，并能有效地控制和抑制相关基因的表达，同时表现出对核酸酶的高抗性。
• Novel nucleoside analogs and oligonucleotide derivatives containing these analogs
  申请人：——

  公开号：US20040192918A1

  公开（公告）日：2004-09-30

  Nucleoside analogues expressed by the following general formula 1 where B represents an aromatic base having carbonyl oxygen at the 2-position, or a 2-hydroxyphenyl group, or oligonucleotide derivatives containing one or more of the nucleoside analogues are provided. The oligonucleotide derivatives are triplex-forming oligonucleotide derivatives which bind specifically to target double-stranded DNA with high affinity in the antigene method to form triplexes, and can thereby control and inhibit the expression of relevant genes efficiently, and which show high resistance to nucleases.

  提供以下通式1所表示的核苷类似物，其中B代表具有2-位置上的羰基氧或2-羟基苯基基团的芳香基，或含有一种或多种核苷类似物的寡核苷酸衍生物。这些寡核苷酸衍生物是三链体形成寡核苷酸衍生物，通过抗基因方法与高亲和力地特异性结合目标双链DNA形成三链体，从而能够高效地控制和抑制相关基因的表达，并表现出高耐核酸酶的特性。
• US7053199B2
  申请人：——

  公开号：US7053199B2

  公开（公告）日：2006-05-30
• Base-pair recognition ability of hydroxyphenyl nucleobases in parallel triplex DNA
  作者：Yoshiyuki Hari、Satoshi Kashima、Hiroyasu Inohara、Shin Ijitsu、Takeshi Imanishi、Satoshi Obika

  DOI：10.1016/j.tet.2013.05.107

  日期：2013.8

  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.