3-Benzoyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione | 210760-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-Benzoyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione
• CAS: 210760-38-6
• 化学式: C₅₂H₄₂N₂O₅
• 分子量: 774.916
• InChiKey: XLYQIUAIRITPLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.26
• 重原子数：
  59.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-1-(bistrityloxymethyl)methyluracil
  参考文献：
  名称：

  Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System

  摘要：

  The synthesis of pyrimidine nucleosides, cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]uracil (4) cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]thymine (5) and cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]cytosine (6) and their corresponding trans isomers is described. Compound 4 showed modest, selective activity against human immunodeficiency virus in acutely infected primary human lymphocytes.

  DOI：

  10.1080/07328319708001358
• 作为产物：
  描述：

  1,3-二(三苯甲氧基)丙-2-醇 、 3-苯甲酰基尿嘧啶 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 3-Benzoyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System

  摘要：

  The synthesis of pyrimidine nucleosides, cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]uracil (4) cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]thymine (5) and cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]cytosine (6) and their corresponding trans isomers is described. Compound 4 showed modest, selective activity against human immunodeficiency virus in acutely infected primary human lymphocytes.

  DOI：

  10.1080/07328319708001358

文献信息

• Ring-Expanded Nucleoside Analogues. 1,3-Dioxan-5-yl Pyrimidines
  作者：Gina Cadet、Ching-See Chan、Rose Y. Daniel、Claudette P. Davis、Deodialsingh Guiadeen、George Rodriguez、Tamara Thomas、Sean Walcott、Peter Scheiner

  DOI：10.1021/jo9715231

  日期：1998.7.1

  1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3-tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N-4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O-2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2,4-triazole derivatives. H-1 NMR data established the conformational preference for equatorial 2'-hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.