9-Acetyl-N²-isobutyrylguanin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-Acetyl-N²-isobutyrylguanin
• 英文别名: 9-acetyl-2-N-isobutyrylguanine；N-(9-acetyl-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide；9-acetyl-N2-isobutyrylguanine；N-(9-Acetyl-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide；N-(9-acetyl-6-oxo-1H-purin-2-yl)-2-methylpropanamide
• 化学式: C₁₁H₁₃N₅O₃
• 分子量: 263.256
• InChiKey: YKJTWNWMCIGITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Acetyl-N²-isobutyrylguanin 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 70.0~100.0 ℃ 、800.0 kPa 条件下， 反应 99.0h， 生成 O6-Benzyl-3',5'-bis-O-(2,4-dichlorobenzyl)guanosin
  参考文献：
  名称：

  神经元祖刚族2'- O-烷基核糖核苷和本征结构的寡核苷酸

  摘要：

  新进入2个' Ø烷基化的核糖核苷和2个'的属性Ø烷基化的寡核糖核苷酸

  DOI：

  10.1002/hlca.19950780219
• 作为产物：
  描述：

  鸟嘌呤 在 4-二甲氨基吡啶 作用下， 生成 9-Acetyl-N²-isobutyrylguanin
  参考文献：
  名称：

  Synthesis of 3-Guaninyl- and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides

  摘要：

  L- And D-glutamic acids, as well as trans-4-hydroxy-L-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

  DOI：

  10.1021/jo2004617

文献信息

• [EN] CYCLOPENTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS<br/>[FR] ANALOGUES DE NUCLÉOSIDE CYCLOPENTYLE UTILISÉS COMME ANTIVIRAUX
  申请人：JANSSEN BIOPHARMA INC

  公开号：WO2020121123A3

  公开（公告）日：2020-07-30
• Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹
  作者：Morris J. Robins、Ruiming Zou、Zhiqiang Guo、Stanislaw F. Wnuk

  DOI：10.1021/jo9617023

  日期：1996.1.1

  Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin-(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethane-sulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-beta-D-ribofuranosyl isomer was shown to be both the kinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.
• CYCLOPENTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS
  申请人：Janssen BioPharma, Inc.

  公开号：EP3894395A2

  公开（公告）日：2021-10-20
• Synthesis of 3-Guaninyl- and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides
  作者：Abdullah Saleh、John G. D’Angelo、Martha D. Morton、Jesse Quinn、Kendra Redden、Rafal W. Mielguz、Christopher Pavlik、Michael B. Smith

  DOI：10.1021/jo2004617

  日期：2011.7.15

  L- And D-glutamic acids, as well as trans-4-hydroxy-L-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.
• Ein neuer Zugang zu 2?-O-Alkylribonucleosiden und Eigenschaften deren Oligonucleotide
  作者：Pierre Martin

  DOI：10.1002/hlca.19950780219

  日期：1995.3.22

  A New Access to 2′-O-Alkylated Ribonucleosides and Properties of 2′-O-Alkylated Oligoribonucleotides

  新进入2个' Ø烷基化的核糖核苷和2个'的属性Ø烷基化的寡核糖核苷酸