3’-O-tert-butyldimethylsilyl-2’-deoxyguanosine | 51549-34-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3’-O-tert-butyldimethylsilyl-2’-deoxyguanosine
• 英文别名: 2-amino-9-[(2R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one；3'-O-(tert-butyldimethylsilyl)-2'-dG；3'-O-tert-butyldimethylsilyl-dG；O^3'-(tert-butyl-dimethyl-silanyl)-2'-deoxy-guanosine；2'-deoxy-3'-O-t-butyldimethylsilylguanosine；2-amino-9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 51549-34-9
• 化学式: C₁₆H₂₇N₅O₄Si
• 分子量: 381.507
• InChiKey: NKDIWLIFGXDOIL-HBNTYKKESA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3’-O-tert-butyldimethylsilyl-2’-deoxyguanosine 在 叔丁基过氧化氢 、 sodium perchlorate monohydrate 、 三氟乙酸吡啶 、 N-methylimidazolium trifluoroacetate 作用下， 以 甲醇 、 正壬烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 48.17h， 生成 2'-脱氧-5-氮杂胞苷酰-(3'→5')-2'-脱氧-鸟苷钠盐
  参考文献：
  名称：

  [EN] IMPROVED PROCESSES FOR THE PREPARATION OF GUADECITABINE AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉS PERFECTIONNÉS DE PRÉPARATION DE GUADÉCITABINE ET D'INTERMÉDIAIRES DE CELLE-CI

  摘要：

  公开号：

  WO2019014286A3
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 咪唑 、 三氯乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 3’-O-tert-butyldimethylsilyl-2’-deoxyguanosine
  参考文献：
  名称：

  [EN] IMPROVED PROCESSES FOR THE PREPARATION OF GUADECITABINE AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉS PERFECTIONNÉS DE PRÉPARATION DE GUADÉCITABINE ET D'INTERMÉDIAIRES DE CELLE-CI

  摘要：

  公开号：

  WO2019014286A3

文献信息

• Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters
  作者：Michele Formica、Tatiana Rogova、Heyao Shi、Naoto Sahara、Branislav Ferko、Alistair J. M. Farley、Kirsten E. Christensen、Fernanda Duarte、Ken Yamazaki、Darren J. Dixon

  DOI：10.1038/s41557-023-01165-6

  日期：2023.5

  Molecules that contain a stereogenic phosphorus atom are crucial to medicine, agrochemistry and catalysis. While methods are available for the selective construction of various chiral organophosphorus compounds, catalytic enantioselective approaches for their synthesis are far less common. Given the vastness of possible substituent combinations around a phosphorus atom, protocols for their preparation

  含有立体磷原子的分子对医学、农业化学和催化至关重要。虽然有多种方法可用于选择性构建各种手性有机磷化合物，但用于其合成的催化对映选择性方法却很少见。鉴于磷原子周围可能存在大量取代基组合，它们的制备方案也应该是不同的，不仅可以轻松获得一种磷化合物，还可以轻松获得多种磷化合物。在这里，我们介绍了一种催化和对映选择性策略，用于制备对映体富集的磷 (V) 中心，该中心可以对映体专一地多样化为各种生物学相关的磷 (V) 化合物。过程，它涉及由超碱性双功能亚氨基正膦催化剂催化的对映选择性亲核取代，可以在磷上容纳各种碳取代基。由此产生的稳定但通用的合成中间体可以与多种医学相关的 O-、N- 和 S 基亲核试剂结合。
• α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT
  作者：Fengting Liang、Nidhi Jain、Troy Hutchens、David D. Shock、William A. Beard、Samuel H. Wilson、M. Paul Chiarelli、Bongsup P. Cho

  DOI：10.1021/jm800692a

  日期：2008.10.23

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.
• Interaction and reactivity of carcinogenic N-acetyl-N-(acyloxy)-2-aminofluorene with deoxyguanosine. An intramolecular approach
  作者：Eric Defrancq、Nadia Pelloux、Anne Leterme、Marie France Lhomme、Jean Lhomme

  DOI：10.1021/jo00016a001

  日期：1991.8

  Solvolysis of 3 in water-acetone mixtures yields the ''adduct'' 4 (65% in water) with product and rate data consistent with the hypothesis that hydrophobic guanine-fluorene stacking, similar to that which occurs when the carcinogenic aminofluorene metabolite is intercalated in DNA, is responsible for selective binding of the carcinogen at the C-8 guanine center.
• LESNIKOWSKI, ZBIGNIEW J.;JAWORSKA-MASLANKA, MARIA M.;STEC, WOJCIECH J., NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 733-736
  作者：LESNIKOWSKI, ZBIGNIEW J.、JAWORSKA-MASLANKA, MARIA M.、STEC, WOJCIECH J.

  DOI：——

  日期：——
• [EN] COMPOUNDS AND METHODS FOR TREATING DISEASE<br/>[FR] COMPOSÉS ET MÉTHODES POUR TRAITER UNE MALADIE
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2023178133A1

  公开（公告）日：2023-09-21

  The invention provides compounds, compositions and methods for treating medical disorders, such as cancer, an autoimmune disorder, and/or a neurological disorder, and inhibiting LINE1 reverse transcriptase and/or HERV-K reverse transcriptase using a compound according to Formula I or a pharmaceutically acceptable salt thereof, or a related compound provided herein.