3'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine | 695183-20-1

• 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'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine
• 英文别名: 3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine；3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)adenosine
• CAS: 695183-20-1
• 化学式: C₂₂H₄₀N₈O₃Si₂
• 分子量: 520.782
• InChiKey: ZVRFBFNMWJNFQK-MXHNKVEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  146.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine 在 N,N'-bis(dimethylaminomethylene)hydrazine 、 5%-palladium/activated carbon 、 氢气 、 对甲苯磺酸 、 triethylamine tris(hydrogen fluoride) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 85.0h， 生成 (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-4-methylsulfonylbutanamide
  参考文献：
  名称：

  A quest for novel antimicrobial targets: Inhibition of Asp-tRNAAsn/Glu-tRNAGln amidotransferase (GatCAB) by synthetic analogs of aminoacyl-adenosine in vitro and live bacteria

  摘要：

  DOI：

  10.1016/j.bioorg.2024.107530
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 sodium tetrahydroborate 、 sodium azide 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine
  参考文献：
  名称：

  [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS
  [FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING

  摘要：

  公开号：

  WO2018138685A3

文献信息

• Synthesis of Stable Aminoacyl-tRNA Analogues Containing Triazole as a Bioisoster of Esters
  作者：Maryline Chemama、Matthieu Fonvielle、Michel Arthur、Jean-Marc Valéry、Mélanie Etheve-Quelquejeu

  DOI：10.1002/chem.200801563

  日期：2009.2.9

  effective synthetic route involving cycloaddition between alkynes and azidonucleosides to afford a new class of stable aminoacyl‐tRNA analogues such as depicted is presented. Biological evaluation showed that theses new compounds act as potent inhibitors of FemXWv aminoacyl transferase, a novel drug target.

  稳定的类似物：提出了一种有效的合成途径，涉及炔烃和叠氮核苷之间的环加成反应，从而提供了一类新的稳定的氨酰基tRNA类似物，如图所示。生物学评估表明，这些新化合物可作为FemX Wv氨酰基转移酶（一种新的药物靶标）的有效抑制剂。
• Synthesis of<i>N</i>⁶-Substituted 3′-Ureidoadenosine Derivatives as Highly Potent Agonists at the Mutant A₃Adenosine Receptor
  作者：Lak Shin Jeong、Seung Ah Choe、Ae Yil Kim、Hea Ok Kim、Zhan-Guo Gao、Kenneth A. Jacobson、Moon Woo Chun、Hyung Ryong Moon

  DOI：10.1080/15257770701493161

  日期：2007.11.26

  Several N6-substituted 3 '-ureidoadenosine derivatives were efficiently synthesized starting from D-glucose for the development of H272E mutant A3 adenosine receptor (AR) agonists. Among compounds tested, 3 '-ureido-N6-(3-iodobenzyl)adenosine (2c) exhibited the highest binding affinity (Ki = 0.22 micro M) at the H272E mutant A3 AR without binding to the natural A3AR.

  从 D-葡萄糖开始有效合成了几种 N6 取代的 3'-脲基腺苷衍生物，用于开发 H272E 突变体 A3 腺苷受体 (AR) 激动剂。在测试的化合物中，3'-ureido-N6-(3-iodobenzyl)adenosine (2c) 在 H272E 突变体 A3 AR 处表现出最高的结合亲和力（Ki = 0.22 micro M），而不与天然 A3AR 结合。
• The Synthesis of Diverse Adenosine 5'-phosphonate Analogues as Chain Terminators against Hepatitis C Virus (HCV)
  作者：Bo-Seung Kim、Beom-Tae Kim、Ki-Jun Hwang

  DOI：10.5012/bkcs.2010.31.6.1643

  日期：2010.6.20

  for synthesis of modified adenosine 5'-phosphonates in which the hydroxyl group at 2' or 3'-position of the sugar moiety is substituted with the azido or amino group and the oxymethyl group at the 4'-position is modified by the ethylene or vinyl group. This synthetic sequence can provide six adenosine 5'-phosphonates via one protocol, and is considered to be very efficient and a convenient route of

  据报道，腺苷 5'-膦酸盐可作为抗丙型肝炎病毒 (HCV) 的潜在链终止剂。因此，我们开发了用于合成修饰的 5'-膦酸腺苷的便捷序列，其中糖部分 2' 或 3'-位的羟基被叠氮基或氨基和 4'-位的氧甲基取代被亚乙基或乙烯基改性。该合成序列可以通过一个方案提供六种腺苷 5'-膦酸盐，被认为是一种非常有效且方便的合成途径。目前正在进行一项针对 HCV 感染的 5'-膦酸腺苷类似物（1、2、3、4、5 和 6）的测定。
• Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase
  作者：Chayada Klinchan、Yu-Ling Hsu、Lee-Chiang Lo、Wanchai Pluempanupat、Pitak Chuawong

  DOI：10.1016/j.tetlet.2014.09.060

  日期：2014.11

  Non-hydrolyzable substrate analogs for tRNA-dependent amidotransferase, 2'- or 3'-aspartyl or -glutamyl adenosine, were synthesized from adenosine without protection of the adenine base. The hydroxyl groups of adenosine were selectively protected, followed by a series of oxidation/reductions to alter the stereochemistry. DFT calculations revealed the driving forces for the ketone hydrate formation at C-2', but not the C-3' carbon during the oxidation step. Subsequently, triflation and azide replacement yielded azidoadenosines, which were coupled to protected amino acids after deprotection and reduction. After global deprotection, the target substrate analogs were obtained in 2-14% overall yields from adenosine. (C) 2014 Elsevier Ltd. All rights reserved.
• WO2019178331A5
  申请人：——

  公开号：WO2019178331A5

  公开（公告）日：2022-03-22