methyl 2,3-di-O-benzoyl-5-bromo-5-deoxy-α-D-ribofuranoside | 120033-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-5-bromo-5-deoxy-α-D-ribofuranoside
• 英文别名: [(2S,3S,4R,5S)-4-benzoyloxy-2-(bromomethyl)-5-methoxyoxolan-3-yl] benzoate
• CAS: 120033-27-4
• 化学式: C₂₀H₁₉BrO₆
• 分子量: 435.271
• InChiKey: LRGXUPZHBLQBKN-VIPLHTEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-5-bromo-5-deoxy-α-D-ribofuranoside 、 methyl 2,3-di-O-benzoyl-5-bromo-5-deoxy-β-D-ribofuranoside 、 乙酸酐 、 盐酸 、 吡啶 以50%的产率得到
  参考文献：
  名称：

  RAJU, NATARAJAN;SMEE, DONALD F.;ROBINS, ROLAND K.;VAGHEFI, MORTEZA M., J. MED. CHEM., 32,(1989) N, C. 1307-1313

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 5-bromo-5-deoxy-D-ribofuranoside 、 苯甲酰氯 以75%的产率得到
  参考文献：
  名称：

  RAJU, NATARAJAN;SMEE, DONALD F.;ROBINS, ROLAND K.;VAGHEFI, MORTEZA M., J. MED. CHEM., 32,(1989) N, C. 1307-1313

  摘要：

  DOI：

文献信息

• Antiviral phosphonate compounds and methods therefor
  申请人：——

  公开号：US20040023921A1

  公开（公告）日：2004-02-05

  Pharmaceutical compositions comprise a nucleotide analog with a phosphonate group at a concentration effective to act as a substrate and/or inhibitor of a viral polymerase, and especially of the HCV RNA dependent RNA polymerase.

  制药组合物包括一种含有膦酸基团的核苷酸类似物，浓度足以作为病毒聚合酶的底物和/或抑制剂，特别是HCV RNA依赖性RNA聚合酶的底物和/或抑制剂。
• Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-.beta.-D-ribofuranosyl analogs of AMP, GMP, IMP, and CMP
  作者：Natarajan Raju、Donald F. Smee、Roland K. Robins、Morteza M. Vaghefi

  DOI：10.1021/jm00126a027

  日期：1989.6

  Methyl 2,3-O-isopropylidene-D-ribofuranoside (1) was converted to 1-O-acetyl-5-bromo-5-deoxy-2,3-di-O-benzoyl-D-ribofuranose (6) in five steps with good yield. The Arbuzov condensation of compound 6 with triethyl phosphite resulted in the synthesis of 1-O-acetyl-2,3-di-O-benzoyl-5-deoxy-5-(diethoxyphosphinyl)-D-ribofuranos e (7). Compound 7 was used for direct glycosylation of both purine and pyrimidine bases. The glycosylation was accomplished with the dry silylated heterocyclic base in the presence of trimethylsilyl triflate. Deblocking of the glycosylation products gave exclusively the beta anomer of the 5'-phosphonate analogues of 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]adenine (13), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]guanosin e (16), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]hypoxant hine (17), and 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]cytosine (15), described here for the first time. The target compounds as well as their intermediates showed no in vitro antiviral or antitumor activity, although phosphorylation of 15 and 16 to di- and triphosphate analogues was demonstrated with use of isolated cellular enzymes.
• US7247621B2
  申请人：——

  公开号：US7247621B2

  公开（公告）日：2007-07-24