5'-O-benzoyl-3'-deoxy-3'-[(benzoyloxy)methyl]-2'-O-acetyl-5-methyluridine | 377084-95-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-benzoyl-3'-deoxy-3'-[(benzoyloxy)methyl]-2'-O-acetyl-5-methyluridine
• 英文别名: [(2S,3R,4R,5R)-4-acetyloxy-2-(benzoyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl benzoate
• CAS: 377084-95-2
• 化学式: C₂₇H₂₆N₂O₉
• 分子量: 522.511
• InChiKey: RJKJPXRDOWVIIT-GBEXAXCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-benzoyl-3'-deoxy-3'-[(benzoyloxy)methyl]-2'-O-acetyl-5-methyluridine 在 sodium methylate 作用下， 以80%的产率得到1-<3-C-(hydroxymethyl)-3-deoxy-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  SYNTHESIS OF NOVELD- ANDL-3′-DEOXY-3′-C-HYDROXYMETHYL NUCLEOSIDE WITH EXOCYCLIC METHYLENE AS POTENTIAL RIBONUCLEOTIDE REDUCTASE INHIBITOR

  摘要：

  D- and L-3'-Deoxy-3'-C-hydroxymethyl thymidine substituted with exocyclic methylene at 2'-position were synthesized, starting from D- and L-xylose as potential ribonucleotide reductase inhibitor, respectively, but they were found to be inactive against several tumor cell lines.

  DOI：

  10.1081/ncn-100002355
• 作为产物：
  描述：

  5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose 在 甲酸 、 三氟甲磺酸三甲基硅酯 作用下， 生成 5'-O-benzoyl-3'-deoxy-3'-[(benzoyloxy)methyl]-2'-O-acetyl-5-methyluridine
  参考文献：
  名称：

  SYNTHESIS OF NOVELD- ANDL-3′-DEOXY-3′-C-HYDROXYMETHYL NUCLEOSIDE WITH EXOCYCLIC METHYLENE AS POTENTIAL RIBONUCLEOTIDE REDUCTASE INHIBITOR

  摘要：

  D- and L-3'-Deoxy-3'-C-hydroxymethyl thymidine substituted with exocyclic methylene at 2'-position were synthesized, starting from D- and L-xylose as potential ribonucleotide reductase inhibitor, respectively, but they were found to be inactive against several tumor cell lines.

  DOI：

  10.1081/ncn-100002355

文献信息

• Synthesis and Structure of Dinucleotides with S-Type Sugar Puckering and Noncanonical ε and ζ Torsion Angle Combination (ν2,ε,ζ-D-CNA)
  作者：Christelle Dupouy、Pierre Lavedan、Jean-Marc Escudier

  DOI：10.1002/ejoc.200701022

  日期：2008.3

  dinucleotide building units of nucleic acids and their (2′,5′)-ν2,ϵ′,ζ′-D-CNA analogues, in which the ϵ and ζ torsional angles are stereocontrolled by a dioxaphosphorinane ring structure (D-CNA family) is described from a common 3-deoxy-3-(hydroxymethyl)-D-allofuranose intermediate. NMR spectroscopic and circular dichroism structure analysis of ν2,ϵ,ζ-D-CNA shows that the sugar puckering is fixed in the C-2′-endo

  核酸的 ν2,ϵ,ζ-D-CNA 二核苷酸结构单元及其 (2',5')-ν2,ϵ',ζ'-D-CNA 类似物的非对映异构体的合成，其中 ϵ 和 ζ扭转角由二氧杂膦环结构（D-CNA 家族）立体控制，描述来自常见的 3-脱氧-3-（羟甲基）-D-异呋喃糖中间体。ν2,ϵ,ζ-D-CNA 的 NMR 光谱和圆二色性结构分析表明，糖褶皱固定在 C-2'-内构象中，并且这些 D-CNA 结构元素可以稳定 ϵ/ζ 扭转角组合，这与典型的 A 型或 B 型双链体中观察到的典型组合显着不同。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)