5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-3-O-formyl-1-O-acetyl-D-ribofuranose | 1032414-32-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-3-O-formyl-1-O-acetyl-D-ribofuranose
• 英文别名: 5-O-benzoyl-3-O-formyl-2-deoxy-2-[(benzoyloxy)methyl]-1-O-acetylribose；5-O-benzoyl-2-deoxy-2-[(benzoyloxy)methyl]-3-O-formyl-1-O-acetyl-D-ribofuranose；[(3R,4S,5R)-2-acetyloxy-5-(benzoyloxymethyl)-4-formyloxyoxolan-3-yl]methyl benzoate
• CAS: 1032414-32-6
• 化学式: C₂₃H₂₂O₉
• 分子量: 442.422
• InChiKey: WYVITDLUYQFJCV-FQAFXWPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-3-O-formyl-1-O-acetyl-D-ribofuranose 在 ammonium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 13.33h， 生成 [(2R,3R,4S,5R)-5-(benzoyloxymethyl)-2-(6-chloropurin-9-yl)-4-(imidazole-1-carbothioyloxy)oxolan-3-yl]methyl benzoate
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  Two ring-expanded analogues (compounds 2 and 3) of the anti-HIV fermentation product oxetanocin A (1) were synthesized from commercially available diacetone D-glucose. Antiviral testing against HIV in ATH8 cells revealed that the ring-expanded analogue 2 possessed a similar activity profile as oxetanocin A. Neither compound, however, was capable of providing full protection to the cells against HIV infection. The isomeric ring-expanded analogue 3 was totally devoid of anti-HIV activity. Molecular modeling suggested that while oxetanocin A and compounds 2 and 3 share a large common substructure with the potent anti-HIV drug, dideoxyadenosine (ddA), the extra hydroxymethyl substituent may contribute negatively to the binding of these molecules to a critical enzyme. The negative contribution may be less important in oxetanocin and isomer 2 than in isomer 3. From these studies it would appear that both oxetane and tetrahydrofuran rings are equivalent templates to support the adenine base in terms of anti-HIV activity.

  DOI：

  10.1021/jm00105a054
• 作为产物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 吡啶 、 盐酸 、 potassium metaperiodate 、 三氯化硼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 41.53h， 生成 5-O-benzoyl-2-deoxy-2-<(benzoyloxy)methyl>-3-O-formyl-1-O-acetyl-D-ribofuranose
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  Two ring-expanded analogues (compounds 2 and 3) of the anti-HIV fermentation product oxetanocin A (1) were synthesized from commercially available diacetone D-glucose. Antiviral testing against HIV in ATH8 cells revealed that the ring-expanded analogue 2 possessed a similar activity profile as oxetanocin A. Neither compound, however, was capable of providing full protection to the cells against HIV infection. The isomeric ring-expanded analogue 3 was totally devoid of anti-HIV activity. Molecular modeling suggested that while oxetanocin A and compounds 2 and 3 share a large common substructure with the potent anti-HIV drug, dideoxyadenosine (ddA), the extra hydroxymethyl substituent may contribute negatively to the binding of these molecules to a critical enzyme. The negative contribution may be less important in oxetanocin and isomer 2 than in isomer 3. From these studies it would appear that both oxetane and tetrahydrofuran rings are equivalent templates to support the adenine base in terms of anti-HIV activity.

  DOI：

  10.1021/jm00105a054

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)
• TSENG, CHRISTOPHER K. -H.;MARGUEZ, VICTOR E.;MILNE, GEORGE W. A.;WYSOCKI,+, J. MED. CHEM., 34,(1991) N, C. 343-349
  作者：TSENG, CHRISTOPHER K. -H.、MARGUEZ, VICTOR E.、MILNE, GEORGE W. A.、WYSOCKI,+

  DOI：——

  日期：——