3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine | 106568-83-6

• 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',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine
• 英文别名: 3',5'-Bis-o-(tert-butyldimethylsilyl)-2'-deoxyinosine；9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 106568-83-6
• 化学式: C₂₂H₄₀N₄O₄Si₂
• 分子量: 480.755
• InChiKey: AIXNFEPWKASLTG-GVDBMIGSSA-N

物化性质

• 沸点：
  566.9±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 O6-(triazol-1-yl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine
  参考文献：
  名称：

  WO2008/45535

  摘要：

  公开号：
• 作为产物：
  描述：

  2'-脱氧腺苷 在 咪唑 、 potassium dihydrogenphosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyinosine
  参考文献：
  名称：

  Synthesis of the Fjord-region cis- and trans-Amino Triol Derivatives of the Carcinogenic Hydrocarbon Benzo[g]chrysene and Utilization for the Synthesis of a Deoxyadenosine Adduct Linked to the N6-Amino Group

  摘要：

  Efficient syntheses of the complete set of four diastereomeric fjord-region amino triol derivatives of benzo[g]chrysene in which the amino group in the 14-position and the adjacent 13-hydroxyl group are trans or cis to one another (trans- and cis-5 and 6) is described. This is the first description of the syntheses of the bay- or fjord-region cis-amino triol derivatives of any carcinogenic polycyclic aromatic hydrocarbon(PAH). The amino triols are key synthetic precursors of PAH-oligonucleotide adducts in which the PAH moiety is covalently linked to the exocyclic amino groups of deoxyadenosine or deoxyguanosine. Formation of adducts of this type via reaction of a PAH diol epoxide metabolite with DNA is believed to be a critical step in the mechanism of PAH carcinogenesis. The synthetic amino triol isomers may be used to synthesize PAH-oligonucleotides needed for site-directed mutagenesis studies to relate isomer structural differences to their effects on DNA replication.

  DOI：

  10.1021/jo00124a027

文献信息

• Wavelength-Selective Uncaging of dA and dC Residues
  作者：Florian Schäfer、Khashti Ballabh Joshi、Manuela A. H. Fichte、Timo Mack、Josef Wachtveitl、Alexander Heckel

  DOI：10.1021/ol200141v

  日期：2011.3.18

  Nitrodibenzofuran (NDBF) groups are used as photolabile “caging” groups to temporarily mask the Watson−Crick interaction of dA and dC residues. They show improved masking capabilities and are photodeprotected 12 times more efficiently than 1-(o-nitrophenyl)-ethyl (NPE) caging groups in these positions. Furthermore, NDBF groups can be removed wavelength-selectively in the presence of NPE groups. This

  硝基二苯并呋喃（NDBF）基团被用作对光不稳定的“笼型”基团，以暂时掩盖dA和dC残基的沃森-克里克相互作用。它们显示出改进的掩蔽能力，并且在这些位置的光脱保护效率比1-（邻硝基苯基）-乙基（NPE）笼蔽基团高12倍。此外，在NPE基团的存在下，NDBF基团可以波长选择性地除去。这将使寡核苷酸具有更复杂的（解笼）策略-超出通常的不可逆触发。
• 3′-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing
  申请人：LaserGen, Inc.

  公开号：US07893227B2

  公开（公告）日：2011-02-22

  Provided are novel nucleotides, nucleoside, and their derivatives described herein, that can be used in DNA sequencing technology and other types of DNA analysis. In one embodiment, the nucleotide or nucleoside with an unprotected 3′-OH group is derivatized at the nucleobase to include a fluorescent dye attached via a linker to a non-cleavable terminating group. The non-cleavable-fluorescent group is designed to terminate DNA synthesis so that DNA oligomers can be sequenced efficiently in a parallel format. These reagents and methods will lead to more accurate identification of polymorphisms and other valuable genetic information.

  提供的是本文描述的新型核苷酸、核苷和它们的衍生物，可用于DNA测序技术和其他类型的DNA分析。在一个实施例中，未保护的3'-OH基团的核苷酸或核苷在核碱基上被衍生，包括通过连接剂连接到不可切断终止基团的荧光染料。不可切断的荧光基团被设计为终止DNA合成，以便DNA寡聚体可以以并行格式高效测序。这些试剂和方法将导致对多态性和其他有价值的遗传信息更准确的识别。
• Azide−Tetrazole Equilibrium of C-6 Azidopurine Nucleosides and Their Ligation Reactions with Alkynes
  作者：Mahesh K. Lakshman、Manish K. Singh、Damon Parrish、Raghavan Balachandran、Billy W. Day

  DOI：10.1021/jo902342z

  日期：2010.4.16

  nucleosides, access to the azido derivatives could be readily attained via displacement of BtO− from the O6-(benzotriazol-1-yl)inosine nucleosides by azide anion. Use of diphenylphosphoryl azide/DBU as a simple route to the acetyl-protected azido nucleosides was also evaluated, but this proved to be inferior. Since these azido nucleosides can exist in an azide·tetrazole equilibrium, the effect of solvent

  已经开发了C-6叠氮嘌呤核糖核苷和2'-脱氧核糖核苷的简便合成方法。对于甲硅烷基和乙酰基保护的以及未受保护的核苷，获得了叠氮基的衍生物，可以很容易地通过BTO的位移达到-从ø 6 -叠氮阴离子（苯并三唑-1-基）肌苷核苷。还评估了使用二苯基磷酰基叠氮化物/ DBU作为获得乙酰基保护的叠氮核苷的简单途径，但事实证明这是较差的。由于这些叠氮基核苷可以在叠氮化物·四唑平衡中存在，因此研究了溶剂极性对该平衡的影响。随后，对Cu介导的叠氮化物-炔（“点击”）连接进行了详细分析。双相CH 2 Cl 2 / H事实证明，2 O介质最适合连接反应，从而抑制了竞争中不希望的叠氮化物还原。有趣的是，尽管在CD 2 Cl 2和CD 2 Cl 2 / D 2中四唑基异构体占主导（约80％）。O，Cu催化的点击反应与甲硅烷基保护的核糖核苷和2'-脱氧核糖核苷顺利进行，从而导致C-6三唑基产物的收率非常好。因此，反应
• Propargylated Purine Deoxynucleosides: New Tools for Fluorescence Imaging Strategies
  作者：Akkaladevi Venkatesham、Sambasiva Rao Pillalamarri、Flore De Wit、Eveline Lescrinier、Zeger Debyser、Arthur Van Aerschot

  DOI：10.3390/molecules24030468

  日期：——

  chemistry reactions take a large share in these events. 5-Ethynyl-2′-deoxyuridine (EdU) is well known for visualizing DNA replication, but does not show any selectivity for incorporation into DNA. Striving for specific visualization of virus replication, in particular HIV replication, a series of propargylated purine deoxynucleosides were prepared aiming for selective incorporation by HIV reverse transcriptase

  生物过程的体内成像是现代细胞生物学的重要资产。这里的选择性反应荧光团是一个重要的工具，点击化学反应在这些事件中占有很大的份额。5-Ethynyl-2'-deoxyuridine (EdU) 以可视化 DNA 复制而闻名，但对掺入 DNA 没有任何选择性。为了实现病毒复制，特别是 HIV 复制的特定可视化，制备了一系列炔丙基化嘌呤脱氧核苷，旨在通过 HIV 逆转录酶 (RT) 选择性掺入。我们在此报告这些核苷类似物的合成和初步生物学效应（细胞毒性、HIV 抑制效应和点击反应的可行性）。
• <i>O</i>⁶-(Benzotriazol-1-yl)inosine Derivatives:  Easily Synthesized, Reactive Nucleosides
  作者：Suyeal Bae、Mahesh K. Lakshman

  DOI：10.1021/ja064682n

  日期：2007.1.1

  additional nucleophile, the released 1-hydroxybenzotriazole undergoes reaction with the formed phosphonium salt leading to the requisite O6-(benzotriazol-1-yl)inosine or 2'-deoxyinosine derivatives. Isolation and characterization of the phosphonium salt as well as analysis by 31P1H} NMR appear to be consistent with this reaction pathway. The resulting O6-(benzotriazol-1-yl)inosine derivatives are effective

  一类新的 O6-(苯并三唑-1-基)肌苷以及相应的 2'-脱氧衍生物可以通过糖保护或未保护的肌苷或 2'-脱氧肌苷核苷与 1H-苯并三唑- 1-基氧基-三（二甲氨基）鏻六氟磷酸盐 (BOP)。该反应似乎是通过核苷鏻盐进行的，并且在没有任何其他亲核试剂的情况下，释放的 1-羟基苯并三唑与形成的鏻盐发生反应，生成必需的 O6-(苯并三唑-1-基)肌苷或 2'-脱氧肌苷衍生物。鏻盐的分离和表征以及 31 P1H} NMR 分析似乎与该反应途径一致。所得的 O6-(苯并三唑-1-基)肌苷衍生物作为亲电子核苷是有效的，与各种亲核试剂如醇、酚、胺和硫醇发生轻松反应。还从 O6-(苯并三唑-1-基)-2'-脱氧肌苷衍生物合成了不寻常且具有挑战性的核苷衍生物，例如芳基桥接二聚体、核苷-氨基酸偶联物和核苷-核苷二聚体。最后，已制备出完全受保护的 DNA 构件 O6-(苯并三唑-1-基)-2'-脱氧肌苷 5'-O-DMT