9-<5'-deoxy-2',3'-di-O-benzoyl-5'-(diethoxyphosphinyl)-β-D-ribofuranosyl>-2-bromohypoxanthine | 120033-37-6

• 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: 9-<5'-deoxy-2',3'-di-O-benzoyl-5'-(diethoxyphosphinyl)-β-D-ribofuranosyl>-2-bromohypoxanthine
• 英文别名: 9-[5'-deoxy-2',3'-di-O-benzoyl-5'-(diethoxyphosphinyl)-β-D-ribofuranosyl]-2-bromohypoxanthine；[(2S,3S,4R,5R)-4-benzoyloxy-5-(2-bromo-6-oxo-3H-purin-9-yl)-2-(diethoxyphosphorylmethyl)oxolan-3-yl] benzoate
• CAS: 120033-37-6
• 化学式: C₂₈H₂₈BrN₄O₉P
• 分子量: 675.429
• InChiKey: SAEOPNOMIDZZDV-PTGPVQHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  160.93
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-<5'-deoxy-2',3'-di-O-benzoyl-5'-(diethoxyphosphinyl)-β-D-ribofuranosyl>-2-bromohypoxanthine 在 palladium on activated charcoal 三甲基溴硅烷 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-.beta.-D-ribofuranosyl analogs of AMP, GMP, IMP, and CMP

  摘要：

  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.

  DOI：

  10.1021/jm00126a027
• 作为产物：
  描述：

  2,3-di-O-benzoyl-5-bromo-5-deoxy-D-ribofuranosyl acetate 在 三氟甲磺酸三甲基硅酯 硫酸氢铵 、 六甲基二硅氮烷 作用下， 反应 82.0h， 生成 9-<5'-deoxy-2',3'-di-O-benzoyl-5'-(diethoxyphosphinyl)-β-D-ribofuranosyl>-2-bromohypoxanthine
  参考文献：
  名称：

  Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-.beta.-D-ribofuranosyl analogs of AMP, GMP, IMP, and CMP

  摘要：

  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.

  DOI：

  10.1021/jm00126a027

文献信息

• An efficient regioselective synthesis of substituted purine analogues of guanosine and inosine
  作者：Natarajan Raju、Roland K. Robins、Morteza M. Vaghefi

  DOI：10.1039/c39890001769

  日期：——

  2-bromo-6-(4-nitrophenylethoxy)purine as the trimethylsilyl derivative (5a) with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose, 1-O-acetyl-2,3-di-O-benzoyl-5-diethoxy-phosphinyl-β-D-ribofuranose, and (2-acetoxythoxy)methyl bromide resulted in N9-regioselective alkylation to give (6a–c), which were then converted to guanine and hypoxanthine nucleosides, nucleotides, and Acyclovir analogues, respectively.

  作为三甲基甲硅烷基衍生物（5a）的2-溴-6-（4-硝基苯基乙氧基）嘌呤与1,2,3,5-四-O-乙酰基-β - D-呋喃核糖，1 - O-乙酰基-2， 3-二-O-苯甲酰基-5-二乙氧基-次膦酰基-β - D-呋喃呋喃糖和（2-乙酰氧基乙氧基）甲基溴导致N 9-区域选择性烷基化，得到（6a – c），然后将其转化为鸟嘌呤和次黄嘌呤核苷，核苷酸和阿昔洛韦类似物。
• RAJU, NATARAJAN;SMEE, DONALD F.;ROBINS, ROLAND K.;VAGHEFI, MORTEZA M., J. MED. CHEM., 32,(1989) N, C. 1307-1313
  作者：RAJU, NATARAJAN、SMEE, DONALD F.、ROBINS, ROLAND K.、VAGHEFI, MORTEZA M.

  DOI：——

  日期：——