N-1-[(2-benzoyloxymethyl)-1,3-dioxan-5-yl]thymine | 191802-83-2

• 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: N-1-[(2-benzoyloxymethyl)-1,3-dioxan-5-yl]thymine
• 英文别名: [5-(5-Methyl-2,4-dioxopyrimidin-1-yl)-1,3-dioxan-2-yl]methyl benzoate
• CAS: 191802-83-2
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: JEJBSSGKBXPVIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-1-[(2-benzoyloxymethyl)-1,3-dioxan-5-yl]thymine 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以0.102 g的产率得到cis-1-[2-(hydroxymethyl)-1,3-dioxan-5-yl]-5-methylpyrimidine-2,4(1H,3H)-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
• 作为产物：
  描述：

  N-3-benzoylthymine 在 氨 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 80.0 ℃ 、266.64 Pa 条件下， 反应 26.5h， 生成 N-1-[(2-benzoyloxymethyl)-1,3-dioxan-5-yl]thymine
  参考文献：
  名称：

  Ring-Expanded Nucleoside Analogues. 1,3-Dioxan-5-yl Pyrimidines

  摘要：

  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.

  DOI：

  10.1021/jo9715231

文献信息

• Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System
  作者：Daniel C. Capaldi、Alessandra Eleuteri、Qin Chen、Raymond F. Schinazi

  DOI：10.1080/07328319708001358

  日期：1997.4

  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.
• 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.