7-(β-D-xylofuranosyl)guanine | 99436-41-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 7-(β-D-xylofuranosyl)guanine
• 英文别名: 2-amino-7-β-D-xylofuranosyl-1,7-dihydro-purin-6-one；7-D-xylofuranosyl-guanin；2-amino-7-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 99436-41-6
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: ZUTSIPKQKRZENB-FTWQFJAYSA-N

物化性质

• 密度：
  2.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  β-D-xylofuranose tetraacetate 在 甲醇 、 苯磺酰胺 、 氨 、 四氯化锡 作用下， 反应 589.5h， 生成 7-(β-D-xylofuranosyl)guanine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹

  摘要：

  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.

  DOI：

  10.1021/jo9617023

文献信息

• Systematic synthesis and biological evaluation of .alpha.- and .beta.-D-xylofuranosyl nucleosides of the five naturally occurring bases in nucleic acids and related analogs
  作者：Gilles Gosselin、Marie Christine Bergogne、Jean De Rudder、Erik De Clercq、Jean Louis Imbach

  DOI：10.1021/jm00152a007

  日期：1986.2

  anomers were obtained by a multistep synthesis with use of 2-amino- or 2-mercapto-alpha-D-xylofuran[1',2':4,5]-2-oxazoline as starting material. The xylofuranosyl nucleosides were tested for their activity against a variety of RNA and DNA viruses and for inhibition of cell growth and macromolecule synthesis. Three compounds, 9-(beta-D-xylofuranosyl)adenine, 9-(beta-D-xylofuranosyl)guanine, and 1-(

  天然存在的核苷的α-和β-D-木呋喃糖基类似物，以及其他D-木呋喃糖基衍生物，已成为其生物学（即抗病毒抗代谢和抑制细胞生长）特性的系统合成和研究对象。通过将嘌呤和嘧啶糖苷配基与过酰化的1-O-乙酰基-α-D-木呋喃糖基糖基化，然后除去保护基团来制备β端基异构体。通过使用2-氨基或2-巯基-α-D-木呋喃[1'，2'：4,5] -2-恶唑啉为起始原料的多步合成法获得α-端基异构体。测试了木呋喃糖基核苷对多种RNA和DNA病毒的活性以及对细胞生长和大分子合成的抑制作用。9-（β-D-木呋喃糖基）腺嘌呤三种化合物
• Stereospecific Synthesis of β-D-Xylofuranosides of Adenine and Guanine
  作者：N. E. Poopeiko、E. I. Kvasyuk、I. A. Mikhailopulo、M. J. Lidaks

  DOI：10.1055/s-1985-34138

  日期：——

  A convenient preparation of the 9-ß-D-xylofuranosides of adenine (xylo-A) and guanine (xylo-G) is described. 1,2-Di-O-acetyl-3,5-Di-O-(p-nitrobenzoyl)-D-xylofuranose is used as the glycosylating agent and a modified procedure for its preparation is given. The method is stereospecific for the ß-anomers.

  描述了一种方便制备腺苷（xylo-A）和鸟苷（xylo-G）的9-β-D-木糖呋喃糖苷的方法。使用1,2-二-O-乙酰基-3,5-二-O-(对硝基苯甲酰基)-D-木糖呋喃糖作为糖苷化试剂，并提供了其制备的改进步骤。该方法对β-异构体具有立体特异性。
• 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.