2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one | 871231-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one
• CAS: 871231-53-7
• 化学式: C₃₁H₃₈N₄O₆Si
• 分子量: 590.751
• InChiKey: YXYLXMLVPSLNMJ-WELLZUMNSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  149.56
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one 在 吡啶 、 N-甲基咪唑 、 四丁基氟化铵 、 氨 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 2-amino-7-[2,3-didehydro-2,3-dideoxy-5-(phenylmethoxyalaninyl)-β-D-ribofuranosyl]-5H-pyrrolo[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2',3'-Didehydro-2',3'-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2',3'-Dideoxy-9-Deazaguanosine and 2',3'-Didehydro-2',3'-Dideoxy-9-Deazainosine

  摘要：

  2',3'-Didehydro-2',3'-dideoxy-9-deazaguanosine (1), its monaphosphate prodrug (2), and two analogues, 2',3'-dideoxy-9-deazaguanosine (3) and 2',3'-didehydro-2',3'-dideoxy-9-deazainosine (4), have been synthesized from benzoylated 9-deazaguanosine (5). Basic hydrolysis of 5, selective protection of the 2-amino and 5'-hydroxy functions with isobulyryl and silyl groups, respectively, followed by reaction with thiocarbonyldiimidazole gave the cyclic thiocarbonate, which, upon reaction with triethyl phosphite, followed 4 deprotection, afforded 1. Treatment of 1 with phenyl methoxyalaninyl phosphochloridate and N-methylimidazole gave 2. Catalytic hydrogenation of 1 gave 3. Hydrodediazoniation of 1 with tert-butyl nitrite and tris(trimethylsilyl)silane gave 4. Compounds 1-4 were found to be inactive against the human immunodeficiency virus and exhibited minimal to no cytotoxic activity against the L1210 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma in vitro.

  DOI：

  10.1081/ncn-200051898
• 作为产物：
  描述：

  (1S,2Xi)-1-(2-氨基-4-氧代-4,7-二氢-1H-吡咯并[3,2-d]嘧啶-7-基)-1,4-脱水-D-苏-戊糖醇 在 咪唑 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2',3'-Didehydro-2',3'-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2',3'-Dideoxy-9-Deazaguanosine and 2',3'-Didehydro-2',3'-Dideoxy-9-Deazainosine

  摘要：

  2',3'-Didehydro-2',3'-dideoxy-9-deazaguanosine (1), its monaphosphate prodrug (2), and two analogues, 2',3'-dideoxy-9-deazaguanosine (3) and 2',3'-didehydro-2',3'-dideoxy-9-deazainosine (4), have been synthesized from benzoylated 9-deazaguanosine (5). Basic hydrolysis of 5, selective protection of the 2-amino and 5'-hydroxy functions with isobulyryl and silyl groups, respectively, followed by reaction with thiocarbonyldiimidazole gave the cyclic thiocarbonate, which, upon reaction with triethyl phosphite, followed 4 deprotection, afforded 1. Treatment of 1 with phenyl methoxyalaninyl phosphochloridate and N-methylimidazole gave 2. Catalytic hydrogenation of 1 gave 3. Hydrodediazoniation of 1 with tert-butyl nitrite and tris(trimethylsilyl)silane gave 4. Compounds 1-4 were found to be inactive against the human immunodeficiency virus and exhibited minimal to no cytotoxic activity against the L1210 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma in vitro.

  DOI：

  10.1081/ncn-200051898