O⁶-phenyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine | 133471-08-6

• 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: O⁶-phenyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-O⁶-phenyl-2'-deoxyinosine；5'-O-(Dimethoxytrityl)-O6-phenyl-2'-deoxyinosine；(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(6-phenoxypurin-9-yl)oxolan-3-ol
• CAS: 133471-08-6
• 化学式: C₃₇H₃₄N₄O₆
• 分子量: 630.7
• InChiKey: WIMNWIIJQYTJGY-WIHCDAFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl phosphorochloridate 、 N,N-二异丙基乙胺 、 O⁶-phenyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到5'-O-(4,4'-dimethoxytrityl)-O⁶-phenyl-2'-deoxyinosine 3'-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite
  参考文献：
  名称：

  Synthesis and characterization of disulfide cross-linked oligonucleotides

  摘要：

  Disulfide cross-linked derivatives of the ''Dickerson/Drew dodecamer'' 5'-d(CGCGAATTCGCG)-3' and the related decamer 5'-d(GCGAATTCGC)-3' have been synthesized, each bearing a dithiobis(ethane) (C2) or dithiobis-(propane) (C3) cross-link at the central adenine (A). NMR and CD spectroscopy indicate that these duplexes are essentially undistorted relative to native B-DNA. However, cross-linking does confer a large degree of stabilization upon the duplexes, as reflected in increased melting temperatures of 15-21-degrees-C for the cross-linked oligonucleotides relative to those for the native sequences. In contrast, un-cross-linked tethers at the same adenines cause substantial decreases in the melting temperature. The cross-linked duplexes were also found to be stable to millimolar concentrations of beta-mercaptoethanol, an important feature for future applications of these cross-links to the study of protein-DNA interactions.

  DOI：

  10.1021/ja00073a016
• 作为产物：
  描述：

  6-chloropurine-2'-deoxyriboside 在 2,6-二甲基吡啶 、 lithium carbonate 、 三乙胺 、 三甲胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O⁶-phenyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine
  参考文献：
  名称：

  A Rapid, High-Yield Method for 5′-Hydroxyl Protection in Very Reactive and Amino Group Modified Nucleosides Using Dimethoxytrityl Tetrafluoroborate

  摘要：

  The conventional method for 4,4'-dimethoxytrityl (DMT) etherification of the 5'-hydroxyl termini in deoxynucleosides that are either highly reactive or those bearing modifications at the exocyclic amino group can be quite problematic, and in several cases the yields are at best mediocre. Herein, we report a rapid, convenient and general procedure for the facile 5'-hydroxyl protection of these nucleosides in exceptionally high yields using DM(+)BF(4)(.). This reagent is particularly useful for the preparation of 5'-O-DMT ethers of nucleosides that are either synthetically valuable or for those that undergo degradation under standard conditions.

  DOI：

  10.1080/07328319608002032

文献信息

• Synthesis and characterization of disulfide cross-linked oligonucleotides
  作者：Ann E. Ferentz、Thomas A. Keating、Gregory L. Verdine

  DOI：10.1021/ja00073a016

  日期：1993.10

  Disulfide cross-linked derivatives of the ''Dickerson/Drew dodecamer'' 5'-d(CGCGAATTCGCG)-3' and the related decamer 5'-d(GCGAATTCGC)-3' have been synthesized, each bearing a dithiobis(ethane) (C2) or dithiobis-(propane) (C3) cross-link at the central adenine (A). NMR and CD spectroscopy indicate that these duplexes are essentially undistorted relative to native B-DNA. However, cross-linking does confer a large degree of stabilization upon the duplexes, as reflected in increased melting temperatures of 15-21-degrees-C for the cross-linked oligonucleotides relative to those for the native sequences. In contrast, un-cross-linked tethers at the same adenines cause substantial decreases in the melting temperature. The cross-linked duplexes were also found to be stable to millimolar concentrations of beta-mercaptoethanol, an important feature for future applications of these cross-links to the study of protein-DNA interactions.
• A Rapid, High-Yield Method for 5′-Hydroxyl Protection in Very Reactive and Amino Group Modified Nucleosides Using Dimethoxytrityl Tetrafluoroborate
  作者：Mahesh K. Lakshman、Barbara Zajc

  DOI：10.1080/07328319608002032

  日期：1996.5

  The conventional method for 4,4'-dimethoxytrityl (DMT) etherification of the 5'-hydroxyl termini in deoxynucleosides that are either highly reactive or those bearing modifications at the exocyclic amino group can be quite problematic, and in several cases the yields are at best mediocre. Herein, we report a rapid, convenient and general procedure for the facile 5'-hydroxyl protection of these nucleosides in exceptionally high yields using DM(+)BF(4)(.). This reagent is particularly useful for the preparation of 5'-O-DMT ethers of nucleosides that are either synthetically valuable or for those that undergo degradation under standard conditions.