9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-O-[(trifluoromethyl)sulfonyl]-β-D-arabinofuranosyl]-9H-purin-6-amine | 118525-22-7

• 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: 9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-O-[(trifluoromethyl)sulfonyl]-β-D-arabinofuranosyl]-9H-purin-6-amine
• 英文别名: Tf(-2)[TBDMS(-3)][TBDMS(-5)]D-Araf(b)-adenin-9-yl；[(2R,3S,4R,5R)-2-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] trifluoromethanesulfonate
• CAS: 118525-22-7
• 化学式: C₂₃H₄₀F₃N₅O₆SSi₂
• 分子量: 627.833
• InChiKey: JTQRKNVZCKAILI-DFYYWFRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-O-[(trifluoromethyl)sulfonyl]-β-D-arabinofuranosyl]-9H-purin-6-amine 在 氟化铵 、 sodium azide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2'-Azido-2'-deoxyadenosine
  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：

  9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-trifluoromethylsulfonyloxy-β-D-arabinofuranosyl]-9H-purin-6-amine 在 4-二甲氨基吡啶 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-O-[(trifluoromethyl)sulfonyl]-β-D-arabinofuranosyl]-9H-purin-6-amine
  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

文献信息

• [EN] CYCLIC DINUCLEOTIDES AS AGONISTS OF STIMULATOR OF INTERFERON GENE DEPENDENT SIGNALLING<br/>[FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DU STIMULATEUR DE LA SIGNALISATION DÉPENDANTE DU GÈNE DE L'INTERFÉRON
  申请人：UNIV TEXAS

  公开号：WO2018156625A1

  公开（公告）日：2018-08-30

  Disclosed herein are new cyclic dinucleotide compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of modulation of immune response to disease, and induce Stimulator of Interferon Genes (STING) dependent type I interferon production and co-regulated genes in a human or animal subject are also provided for the treatment diseases such as cancer, particularly metastatic solid tumors and lymphomas, inflammation, allergic and autoimmune disease, infectious disease, and for use as anti-viral agents and vaccine adjuvants.

  本文披露了新的环二核苷酸化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了调节免疫应答以及诱导干扰素基因激活剂（STING）依赖型I干扰素在人类或动物受试者中产生和共调控基因的方法，用于治疗癌症、尤其是转移性实体瘤和淋巴瘤、炎症、过敏和自身免疫疾病、传染病，以及作为抗病毒剂和疫苗佐剂的用途。
• Deoxygenative [1,2]-Hydride Shift Rearrangements in Nucleoside and Sugar Chemistry:  Analogy with the [1,2]-Electron Shift in the Deoxygenation of Ribonucleotides by Ribonucleotide Reductases¹
  作者：Morris J. Robins、Ireneusz Nowak、Stanislaw F. Wnuk、Fritz Hansske、Danuta Madej

  DOI：10.1021/jo071102b

  日期：2007.10.1

  semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an “orchestrated” [1,2]-hydride shift with departure of a leaving group from the opposite face. Transient formation of a CO group is followed by rapid transfer of a hydride-equivalent from the same face from which the leaving group departed

  在我们的实验室中观察到的半频哪醇重排的变体已应用于几种呋喃糖和吡喃糖衍生物的合成。该过程包括“精心策划的” [1,2]氢化物转移，同时离去基团从相反的表面离开。瞬态形成C O基团后，从离去基团离开的同一面快速转移氢化物当量，这导致两个邻位碳原子处的立体化学两次反转。2'治疗ö -和3'- ö -tosyladenosine与三乙基硼锂在DMSO / THF给出了与β-相应2'-和3'-脱氧核苷类似物d -苏型配置。相同的5'- O处理-TPS -2'- ö -tosyladenosine得到9-（5- ö -TPS-2-脱氧β- d -苏-pentofuranosyl）腺嘌呤。5'-OH和5'- O - TPS化合物具有相同的[1,2]-氢化物位移和立体化学，表明不存在远端羟基参与。将该方法应用于其他核苷2'- O-甲苯磺酰基衍生物，以良好的收率得到了2'-脱氧苏糖基化合物。对于2'- O