2,3-dideoxy-5-O-(4-methylbenzoyl)-5-methoxymethylcytidine | 133697-48-0

• 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: 2,3-dideoxy-5-O-(4-methylbenzoyl)-5-methoxymethylcytidine
• 英文别名: Cytidine, 2',3'-dideoxy-5-(methoxymethyl)-, 5'-(4-methylbenzoate)；[(2S,5R)-5-[4-amino-5-(methoxymethyl)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 133697-48-0
• 化学式: C₁₉H₂₃N₃O₅
• 分子量: 373.409
• InChiKey: LGDPJGNJKYBJJW-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-5-O-(4-methylbenzoyl)-5-methoxymethylcytidine 、 氨 生成 2',3'-dideoxy-5-methoxymethylcytidine
  参考文献：
  名称：

  ABDEL-MEGIED, AHMED E. -S.;PEDERSEN, ERIK B.;NIELSEN, CARSTEN M., MONATSH. CHEM., 122,(1991) N-2, C. 59-70

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Methyl-benzoic acid (S)-5-(5-methoxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 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-methoxymethylcytidine
  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

文献信息

• ABDEL-MEGIED, AHMED E. -S.;PEDERSEN, ERIK B.;NIELSEN, CARSTEN M., MONATSH. CHEM., 122,(1991) N-2, C. 59-70
  作者：ABDEL-MEGIED, AHMED E. -S.、PEDERSEN, ERIK B.、NIELSEN, CARSTEN M.

  DOI：——

  日期：——
• Synthesis of 2?,3?-dideoxynucleosides from 5-alkoxymethyluracils
  作者：Ahmed E. -S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1007/bf00815166

  日期：——

  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).