[(2S,5R)-5-[2,4-dioxo-5-(pentoxymethyl)pyrimidin-1-yl]oxolan-2-yl]methyl 4-methylbenzoate | 133635-58-2

• 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,5R)-5-[2,4-dioxo-5-(pentoxymethyl)pyrimidin-1-yl]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 133635-58-2；133697-40-2
• 化学式: C₂₃H₃₀N₂O₆
• 分子量: 430.501
• InChiKey: HSKYUTDJWUKGFD-XJDOXCRVSA-N

物化性质

• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(2S,5R)-5-[2,4-dioxo-5-(pentoxymethyl)pyrimidin-1-yl]oxolan-2-yl]methyl 4-methylbenzoate 在 ammonium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 2',3'-dideoxy-5-O-(4-methylbenzoyl)-5-pentyloxymethylcytidine
  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：

  (S)-γ-(4-methylbenzoyloxymethyl)-γ-butyrolactone 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 [(2S,5R)-5-[2,4-dioxo-5-(pentoxymethyl)pyrimidin-1-yl]oxolan-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