2'-azido-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)adenosine | 695183-22-3

• 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'-azido-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)adenosine
• 英文别名: 9-((2R,3R,4S,5R)-3-azido-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine；2'-azido-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-adenosine；9-[(2R,3R,4S,5R)-3-azido-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-amine
• CAS: 695183-22-3
• 化学式: C₂₂H₄₀N₈O₃Si₂
• 分子量: 520.782
• InChiKey: NFPQVVWHAMXHGL-MXHNKVEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-azido-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)adenosine 在 氟化铵 、 palladium on carbon 、 氢气 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成
  参考文献：
  名称：

  Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.09.060
• 作为产物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium azide 、 戴斯-马丁氧化剂 、 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 52.0h， 生成 2'-azido-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)adenosine
  参考文献：
  名称：

  Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.09.060

文献信息

• [EN] CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS<br/>[FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019046500A1

  公开（公告）日：2019-03-07

  The present invention is directed to compounds of the formula (I) wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及式(I)的化合物，其中所有取代基均在此定义，以及包括本发明化合物的药学上可接受的组合物和使用该组合物治疗各种疾病的方法。
• 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。
• 10.1016/j.bioorg.2024.107530
  作者：Sangsuwan, Withsakorn、Taweesablamlert, Amata、Boonkerd, Anon、Isarangkool Na Ayutthaya, Chawarat、Yoo, Sion、Javid, Babak、Faikhruea, Kriangsak、Vilaivan, Tirayut、Aonbangkhen, Chanat、Chuawong, Pitak

  DOI：10.1016/j.bioorg.2024.107530

  日期：——
• 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.