((2S)-5-(4-amino-5-(sec-butoxymethyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate | 133635-69-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: ((2S)-5-(4-amino-5-(sec-butoxymethyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate
• CAS: 133635-69-5
• 化学式: C₂₂H₂₉N₃O₅
• 分子量: 415.489
• InChiKey: QOJOSIVADANZDK-OBONGRFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.67
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2S)-5-(4-amino-5-(sec-butoxymethyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate 在 氨 作用下， 以14%的产率得到2',3'-dideoxy-5-(1-methylpropoxymethyl)cytidine
  参考文献：
  名称：

  Synthesis of 2?,3?-dideoxynucleosides from 5-alkoxymethyluracils

  摘要：

  A modified synthesis of protected 2,3-dideoxyribose 5 starting from L-glutamic acid (1) is described. Reaction of 5 with silylated 5-hydroxymethyluracil 7 a and 5-alkoxymethyluracils 7 b-e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2',3'-dideoxyuridine derivatives 8 a-e and 9 a-e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides 10 a-e and 11 a-e. Treatment of 9 b-e with tri(1H-1,2,4-triazol-1-yl) phosphine oxide and subsequent reaction of 12 b-e with ammonia in dioxane afforded the cytosine derivatives 13 b-e which on treatment with methanolic ammonia gave the corresponding 2',3'-dideoxycytidine derivatives 14 b-e and 15 b-e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).

  DOI：

  10.1007/bf00815166
• 作为产物：
  描述：

  methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside 在 ammonium hydroxide 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 ((2S)-5-(4-amino-5-(sec-butoxymethyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate
  参考文献：
  名称：

  Synthesis of 2?,3?-dideoxynucleosides from 5-alkoxymethyluracils

  摘要：

  A modified synthesis of protected 2,3-dideoxyribose 5 starting from L-glutamic acid (1) is described. Reaction of 5 with silylated 5-hydroxymethyluracil 7 a and 5-alkoxymethyluracils 7 b-e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2',3'-dideoxyuridine derivatives 8 a-e and 9 a-e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides 10 a-e and 11 a-e. Treatment of 9 b-e with tri(1H-1,2,4-triazol-1-yl) phosphine oxide and subsequent reaction of 12 b-e with ammonia in dioxane afforded the cytosine derivatives 13 b-e which on treatment with methanolic ammonia gave the corresponding 2',3'-dideoxycytidine derivatives 14 b-e and 15 b-e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).

  DOI：

  10.1007/bf00815166