2',3',5'-tris-O-[tert-butyl(dimethyl)silyl]-5-iodocytidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tris-O-[tert-butyl(dimethyl)silyl]-5-iodocytidine
• 英文别名: 1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-2-yl]-4-imino-5-iodo-pyrimidin-2-one；4-amino-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-iodopyrimidin-2-one
• 化学式: C₂₇H₅₄IN₃O₅Si₃
• 分子量: 711.904
• InChiKey: HJZKIBHFMSMROG-YYTDSSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',3',5'-tris-O-[tert-butyl(dimethyl)silyl]-5-iodocytidine 在 吡啶 、 氨 、 sodium hydride 、 lead dioxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties

  摘要：

  5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.080

文献信息

• Synthesis and photophysics of a porphyrin–fullerene dyad assembled through Watson–Crick hydrogen bonding
  作者：Jonathan L. Sessler、Janarthanan Jayawickramarajah、Andreas Gouloumis、Tomás Torres、Dirk M. Guldi、Stephen Maldonado、Keith J. Stevenson

  DOI：10.1039/b418345b

  日期：——

  A novel porphyrin–fullerene dyad assembled through Watson–Crick hydrogen bonds is described; this system undergoes photoinduced electron transfer upon irradiation with visible light to produce a charge separated state that is substantially longer lived than that of previous dyads of this type.

  描述了通过沃森克里克氢键组装的新型卟啉富勒烯二元体；该系统在可见光照射下发生光致电子转移，产生电荷分离状态，其寿命比以前的此类成对体的寿命要长得多。
• Design, Synthesis, and Self-Assembly of “Artificial Dinucleotide Duplexes”
  作者：Jonathan L. Sessler、Ruizheng Wang

  DOI：10.1021/jo980194p

  日期：1998.6.1

  The synthesis of the A-U and G-C functionalized systems 1, 2, 3, and 4 has been accomplished using palladium-mediated cross-coupling reactions. These systems undergo self-association in nonpolar solvents such as CDCl3 as judged from FABMS and NMR spectroscopic analyses.
• Hydrogen-Bond-Mediated Photoinduced Electron-Transfer:  Novel Dimethylaniline−Anthracene Ensembles Formed via Watson−Crick Base-Pairing
  作者：Jonathan L. Sessler、Muhunthan Sathiosatham、Christopher T. Brown、Timothy A. Rhodes、Gary Wiederrecht

  DOI：10.1021/ja005547s

  日期：2001.4.1

  The synthesis of a new, noncovalent anthracene-dimethylaniline dyad (ensemble I) held together via guanosine-cytidine Watson-Crick base-pairing interactions is reported. Upon excitation at 420 nm, photoinduced electron-transfer from the dimethylaniline donor to the singlet excited state of the anthracene acceptor occurs, as inferred from a combination of time-resolved fluorescence quenching and transient absorption measurements. In toluene at room temperature, the rate constants for photoinduced intraensemble electron-transfer and subsequent back-electron-transfer (charge recombination) are k(CS) = (3.5 +/- 0.03) x 10(10) s(-1) and k(CR) = (1.42 +/- 0.03) x 10(9) s(-1), respectively.
• Novel Guanosine−Cytidine Dinucleoside that Self-Assembles into a Trimeric Supramolecule
  作者：Jonathan L. Sessler、Janarthanan Jayawickramarajah、Muhunthan Sathiosatham、Courtney L. Sherman、Jennifer S. Brodbelt

  DOI：10.1021/ol034765y

  日期：2003.7.1

  [GRAPHICS]Synthesis and assembly studies of a guanosine-cytidine dinucleoside 1 that self-assembles into a trimeric supramolecule (1) are presented. Dinucleoside 1 was obtained by utilizing two consecutive palladium-catalyzed cross-coupling reactions. Ensemble I was analyzed by ESI-MS, NMR spectroscoples, size exclusion chromatography (SEC), and vapor pressure osmometry (VPO).
• Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties
  作者：Mariko Aso、Yasuhiro Matsui、Bo Yang、Midori Sasagaki、Daiki Okado、Kazuteru Usui、Noboru Koga、Hiroshi Suemune

  DOI：10.1016/j.tet.2015.05.080

  日期：2015.8

  5-N-tert-Butylaminoxylcytidine was synthesized as a new spin-labelled cytidine to detect guanosine by EPR spectroscopy. Metal-halogen exchange reaction of TBS-protected N-benzoyl-5-iodocytidine followed by a reaction with 2-methyl-2-nitrosopropane afforded 5-N-tert-butylhydroxylaminocytidine with considerable affinity for guanosine and its oxidation gave 5-N-tert-butylaminoxylcytidine. Changes in EPR parameters monitored its selective base pairing with guanosine derivatives and the formation of a 2:2 complex with 8-oxoguanosine. (C) 2015 Elsevier Ltd. All rights reserved.