methyl 3-azido-2,3-dideoxy-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside | 149437-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-azido-2,3-dideoxy-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside
• 英文别名: [(2S,3S,5S)-3-azido-5-methoxyoxolan-2-yl]methyl 4-phenylbenzoate
• CAS: 149437-42-3
• 化学式: C₁₉H₁₉N₃O₄
• 分子量: 353.378
• InChiKey: HDTWFGHOLMTLIM-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(3-azido-2,3-dideoxy-α,β-D-erythro-pentafuranosyl)-5-(4-(2-hydroxyethyl)piperazinomethyl)uracil
  参考文献：
  名称：

  Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

  摘要：

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.

  DOI：

  10.1007/bf00808509
• 作为产物：
  描述：

  methyl 2,3-dideoxy-3-iodo-5-O-(4-phenylbenzoyl)-α-D-threo-pentofuranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到methyl 3-azido-2,3-dideoxy-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside
  参考文献：
  名称：

  Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

  摘要：

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.

  DOI：

  10.1007/bf00808509

文献信息

• Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents
  作者：Mohammed S. Motawia、Per T. Jørgensen、Anni Larnkjær、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808509

  日期：1993.1

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.