2′,3′,5′-tri-O-(tert-butyldimethylsilyl)-5-iodo-uridine | 146645-06-9

• 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′-tri-O-(tert-butyldimethylsilyl)-5-iodo-uridine
• 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]-5-iodo-pyrimidine-2,4-dione；1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 146645-06-9
• 化学式: C₂₇H₅₃IN₂O₆Si₃
• 分子量: 712.889
• InChiKey: JEVRXFJEOXKKDH-YYTDSSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 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：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2′,3′,5′-tri-O-(tert-butyldimethylsilyl)-5-iodo-uridine 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 1-[4-hydroxy-5-ethynyl-1-(2',3',5'-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)pyrimidin-2-one]-8-[6-amino-8-ethynyl-9-(2',3',5'-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)purine]anthracene
  参考文献：
  名称：

  Design, Synthesis, and Self-Assembly of “Artificial Dinucleotide Duplexes”

  摘要：

  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.

  DOI：

  10.1021/jo980194p
• 作为产物：
  描述：

  2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine 在 碘 作用下， 以 乙腈 为溶剂， 以86%的产率得到2′,3′,5′-tri-O-(tert-butyldimethylsilyl)-5-iodo-uridine
  参考文献：
  名称：

  嘧啶碱基及其核苷在细胞内的间接电化学卤化为5-卤代衍生物

  摘要：

  阳极产生的“ hal”物种（Lix或Bu 4 NX，LiClO 4，MeCN，Pt / Pt； I 2，LiClO 4，MeCN）与嘧啶碱基及其核苷的反应可产生高收率的5卤代化合物

  DOI：

  10.1016/0040-4039(93)88044-j

文献信息

• Stereoselective Synthesis of Highly Functionalized Arabinosyl Nucleosides through Application of an <i>N</i>-Nitro Protecting Group
  作者：David H. Hilko、Laurent F. Bornaghi、Sally-Ann Poulsen

  DOI：10.1021/acs.joc.8b01834

  日期：2018.10.5

  3-N-nitro group by reductive nitration (zinc metal in acetic acid, 5 min) and the silyl protecting groups of the alkyne and 3′,5′ hydroxyls (fluoride reagent, 16 h) was established as the final synthetic step. This application of the 3-N-nitro protecting group addresses the significant shortfalls of the conventional approach to synthesis of 2′ modified nucleosides, wherein condensation of a 2′ modified

  从2'，3'，5'-tri的6个步骤合成了在C2'带有卤素（Cl，Br或I）和在C5带有乙炔基的2'-脱氧-2'，5-二取代的阿拉伯糖基尿苷衍生物- ø -乙酰基-5-碘尿苷在61％（化合物的总产率3，Cl）的，47％（化合物4，Br）和19％（化合物5，I）。稳定2'- O- triflyl离去基团中间体以克服自发的分子内2,2'-脱水尿苷的形成对于合成至关重要。具体来说，赞成S N在分子内环化作用下与卤素亲核体反应2，通过在N-3处引入相邻的吸电子硝基取代基降低了O-2氧的亲核性。3- N-硝基的引入迅速进行（三氟乙酸硝鎓，1分钟），并以定量产率进行。采用一锅法通过还原硝化（乙酸中的锌金属，5分钟）和炔烃和3'，5'羟基的甲硅烷基保护基（氟化试剂，16 h）除去3- N-硝基的方法是确定为最终的合成步骤。3- N-硝基保护基团解决了合成2'修饰核苷的常规方法的重大缺陷，其中2'修饰糖片
• Two‐Factor Fluorogenicity of Tetrazine‐Modified Cyanine‐Styryl Dyes for Bioorthogonal Labelling of DNA
  作者：Philipp Geng、Eileen List、Franziska Rönicke、Hans‐Achim Wagenknecht

  DOI：10.1002/chem.202203156

  日期：2023.2.7

  electron demand Diels-Alder reactions of the synthetic tetrazine-modified dyes with bicyclononyne-modified DNA follow the new concept of the two-factor fluorescence fluorogenicity which improves the signal-to-noise ratio such that washing procedures prior to cell imaging are not needed. The labelling reactions proceed also extremely fast.

  又快又亮！合成四嗪修饰染料与双环壬酮修饰 DNA 的逆电子需求 Diels-Alder 反应遵循双因子荧光荧光性的新概念，提高了信噪比，使得细胞成像之前的洗涤程序不需要。标记反应也进行得非常快。
• In-cell indirect electrochemical halogenation of pyrimidine bases and their nucleosides to 5-haloderivatives
  作者：G. Palmisano、B. Danieli、M. Santagostino、B. Vodopivec、G. Fiori

  DOI：10.1016/0040-4039(93)88044-j

  日期：1992.12

  Reaction of anodically generated “halonium” species (Lix or Bu4NX, LiClO4, MeCN, Pt/Pt; I2, LiClO4, MeCN ) with pyrimidine bases and their nucleosides leads to 5-halo compounds in good yields

  阳极产生的“ hal”物种（Lix或Bu 4 NX，LiClO 4，MeCN，Pt / Pt； I 2，LiClO 4，MeCN）与嘧啶碱基及其核苷的反应可产生高收率的5卤代化合物
• 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.