(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate | 107698-78-2

• 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: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• 英文别名: 1-[2',3',5'-tri-O-acetyl-β-D-ribo-pentofuranosyl]-2-N-isobutyrylguanine；2',3',5'-tri-O-acetyl-2-N-isobutyrylguanosine；9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-N2-isobutanoylguanine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 107698-78-2
• 化学式: C₂₀H₂₅N₅O₉
• 分子量: 479.447
• InChiKey: YQSNJEPVDDEJNE-QEPJRFBGSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 在 sodium methylate 、 硝酸胍 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到1-[5'-O-acetyl-β-D-ribo-pentofuranosyl]-2-N-isobutyrylguanine
  参考文献：
  名称：

  过酰基化核糖核苷的选择性脱酰

  摘要：

  已经开发出用于N，O-酰化核糖核苷的化学选择性脱保护的方案。在0°C下于MeOH / CH 2 Cl 2中于硝酸胍和NaOMe中进行过酰化的嘧啶核糖核苷进行高产率的O-脱酰化，而由于保留了O5'-酰基，因此在过酰化的嘌呤核糖核苷中观察到的化学选择性更高。核碱基保护基团（A Bz，C Bz，G iBu和U Bz）在这些条件下稳定，使该试剂混合物成为收集核苷化学中保护基方案的宝贵补充。

  DOI：

  10.1016/j.tetlet.2009.01.147
• 作为产物：
  描述：

  2',3',5'-tri-O-acetyl-6-O-benzyl-2-N-isobutyrylguanosine 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以95%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  ¹⁵N Double-Labeled Guanosine from Inosine through Ring-Opening−Ring-Closing and One-Pot Pd-Catalyzed C−O and C−N Cross-Coupling Reactions

  摘要：

  [N,1-N-15(2)]-Guanosine, or [1,NH2-N-15(2)]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with (NH2OH)-N-15, followed by conversion of the N-15-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and (PhCONH2)-N-15 or (PrCONH2)-Pr-i-N-15 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.

  DOI：

  10.1021/jo100808w

文献信息

• Direct Minisci-Type C–H Amidation of Purine Bases
  作者：David T. Mooney、Peter R. Moore、Ai-Lan Lee

  DOI：10.1021/acs.orglett.2c03206

  日期：2022.11.4

  Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically

  已开发出一种嘌呤的 C-H 羧基酰胺化方法，该方法能够直接安装伯、仲和叔酰胺。以前对嘌呤的 Minisci 型研究仅限于烷基化和芳基化。在此，我们提出了第一种对多种嘌呤进行直接 C-H 酰胺化的方法：黄嘌呤、鸟嘌呤和腺嘌呤结构，包括鸟苷和腺苷型核苷。Minisci 型反应还不含金属、便宜、操作简单、可扩展，适用于生物学重要分子的后期功能化。
• Biocatalytic Separation of <i>N</i>-7/<i>N</i>-9 Guanine Nucleosides
  作者：Sunil K. Singh、Vivek K. Sharma、Carl E. Olsen、Jesper Wengel、Virinder S. Parmar、Ashok K. Prasad

  DOI：10.1021/jo101565e

  日期：2010.11.19

  Vorbruggen coupling of trimethylsilylated 2-N-isobutanoylguanine with peracetylated pentofuranose derivatives generally gives inseparable N-7/N-9 glycosyl mixtures We have shown that the two isomers can be separated biocatalytically by Novozyme-435-mediated selective deacetylation of the 5'-O-acetyl group of peracetylated N-9 guanine nucleosides
• ROZNERS, EH. Z.;REKIS, A. X.;KUMPINSH, V. X.;BIZDENA, EH. O., BIOORGAN. XIMIYA, 16,(1990) N1, S. 1531-1536
  作者：ROZNERS, EH. Z.、REKIS, A. X.、KUMPINSH, V. X.、BIZDENA, EH. O.

  DOI：——

  日期：——
• GDANIEC, Z.;MIELEWCZYK, S.;ADAMIAK, R. W., BIOPHOSPHAT. AND ARALOGUES: SYNTH., STRUCT., METAB. AND ACTIV. PROC. 2ND +
  作者：GDANIEC, Z.、MIELEWCZYK, S.、ADAMIAK, R. W.

  DOI：——

  日期：——