2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine | 72409-24-6

• 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: 2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine
• 英文别名: 2',3',5'-O-tris(tert-butyldimethylsilyl)guanosine；TBDMS(-2)[TBDMS(-3)][TBDMS(-5)]Ribf(b)-guanin-9-yl；2-amino-9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 72409-24-6
• 化学式: C₂₈H₅₅N₅O₅Si₃
• 分子量: 626.032
• InChiKey: AMSWKXJXTYPJKN-UMCMBGNQSA-N

物化性质

• 熔点：
  288-290 °C(Solv: hexane (110-54-3))
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2',3'-O-bis[(tert-butyl)dimethylsilyl]-2-N-(4,4'-dimethoxytrityl)guanosine
  参考文献：
  名称：

  Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity

  摘要：

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.021
• 作为产物：
  描述：

  N2-异丁酰基鸟苷一水合物 在 咪唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine
  参考文献：
  名称：

  核苷酸，XVIII。合成和本征化学合成（叔丁基二甲基甲硅烷基）鸟苷，鸟苷3'-磷酸甘油和鸟苷-卤代寡核苷† ‡

  摘要：

  核苷酸，十八。（叔丁基二甲基甲硅烷基）鸟苷，鸟苷-3'-磷酸三酯和含鸟苷的寡核苷酸的合成及性能

  DOI：

  10.1002/hlca.19830660718

文献信息

• [EN] COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF<br/>[FR] COMPOSÉS COMPRENANT UN LIEUR CLIVABLE ET LEURS UTILISATIONS
  申请人：INTOCELL INC

  公开号：WO2019008441A1

  公开（公告）日：2019-01-10

  Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a SO2 functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

  提供了一种包括可切割连接物的化合物，其用途，以及用于制备该化合物的中间体化合物，更具体地，本发明的包括可切割连接物的化合物可能包括具有特定功能或活性的活性剂（例如，药物，毒素，配体，用于检测的探针等），能够选择性释放活性剂的SO2官能团，以及通过外部刺激触发化学反应，物理化学反应和/或生物反应的官能团，并且还可以包括具有与所需靶受体结合特异性的配体（例如，寡肽，多肽，抗体等）。
• Mechanistic studies in the synthesis of a series of thieno-expanded xanthosine and guanosine nucleosides
  作者：Zhibo Zhang、Orrette R. Wauchope、Katherine L. Seley-Radtke

  DOI：10.1016/j.tet.2008.09.011

  日期：2008.11

  During the synthetic pursuit of guanosine (triG) and xanthosine (triX) tricyclic nucleosides analogues, an interesting side product was discovered. In an effort to uncover the mechanistic factors leading to this result, a series of reaction conditions were investigated. It was found that by varying the conditions, the appearance of the side product could be controlled. In addition, the yield of the

  在鸟苷 (triG) 和黄苷 (triX) 三环核苷类似物的合成过程中，发现了一种有趣的副产物。为了揭示导致这一结果的机械因素，研究了一系列反应条件。发现通过改变条件，可以控制副产物的出现。此外，可以控制所需产物的产量，以提供 triG 和 triX 的 50:50 混合，或其中一种或另一种的大部分。为了证明该方法的广泛实用性，它还适用于从 5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺 (AICAR) 合成鸟苷和黄苷。本文报告了围绕合成工作的机制细节。
• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS<br/>[FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES UTILISÉS COMME AGONISTES STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019125974A1

  公开（公告）日：2019-06-27

  A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类具有通用公式（I）的多环化合物的类别，其中Base1，Base2，Y，Za，Xa，Xa1，Xb，Xb1，Xc，Xc1，Xd，Xd1，R1，R1a，R2，R2a，R3，R4，R4a，R5，R6，R6a，R7，R7a，R8，R8a和R9按本说明书中定义，可能对作为I型干扰素产生的诱导剂特别有用，具体作为STING激活剂。还提供了合成和使用化合物的过程。
• Solventless Protocol for Efficient Bis-<i>N</i>-Boc Protection of Adenosine, Cytidine, and Guanosine Derivatives
  作者：Siddharth A. Sikchi、Philip G. Hultin

  DOI：10.1021/jo060430t

  日期：2006.8.1

  A solvent-free reaction employing a simple low-energy ball mill apparatus converts the amino groups of adenosine, 2-deoxyadenosine, cytidine, 2-deoxycytidine, guanosine, and 2-deoxyguanosine as well as some of their ribosyl O-protected derivatives to the corresponding bis-N-Boc carbamates. In the case of guanosine compounds, the carbonyl group of the base moiety was also blocked as its O-Boc enol carbonate

  使用简单的低能球磨仪进行的无溶剂反应将腺苷，2-脱氧腺苷，胞嘧啶核苷，2-脱氧胞苷，鸟苷和2-脱氧鸟苷的氨基以及它们的一些核糖基O保护的衍生物转化为相应的bis- N -Boc氨基甲酸酯。在鸟苷化合物的情况下，该碱基部分的羰基也被封闭为其O- Boc烯醇碳酸酯。使用瞬态原位O硅烷化的这种方法的一种变体允许制备bis- N-Boc核苷，其中糖羟基不受保护。除鸟苷化合物外，球磨反应迅速，方便且产率很高。这种高效的方法使用适合进一步合成操作的碱稳定且酸不稳定的基团保护这些核苷的氨基。
• Microwave-Assisted Direct Amination: Rapid Access to Multi-Functionalized N6-Substituted Adenosines
  作者：Trent D. Ashton、Peter J. Scammells

  DOI：10.1071/ch07340

  日期：——

  Analogues of adenosine have a range of interesting biological activities and potential therapeutic applications. A method for the efficient preparation of highly functionalized N6-substituted adenosines has been developed from the corresponding tert-butyldimethylsilyl-protected inosine. The key step in this procedure is a microwave-assisted amination reaction between an appropriately substituted inosine and an amine in the presence of PyBroP. High yields of desired N6-substituted adenosines were achieved with hindered amines and the reaction was also found to accommodate a range of substituents on the inosine precursor.

  腺苷的类似物具有一系列有趣的生物活性和潜在的治疗用途。从相应的叔丁基二甲基硅基保护肌苷出发，我们开发出了一种高效制备高官能度 N6 取代腺苷的方法。该方法的关键步骤是在 PyBroP 的存在下，在适当取代的肌苷和胺之间进行微波辅助胺化反应。使用受阻胺可以获得高产率的所需 N6 取代腺苷，而且该反应还能适应肌苷前体上的一系列取代基。