1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-tert-butoxycarbonylmethylthymine | 799261-97-5

• 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: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-tert-butoxycarbonylmethylthymine
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[5-methyl-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl benzoate
• CAS: 799261-97-5
• 化学式: C₃₇H₃₆N₂O₁₁
• 分子量: 684.7
• InChiKey: IQACFDJAWIPHIW-SSKIFPDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-tert-butoxycarbonylmethylthymine 在 吡啶 、 氯化亚砜 、 resin-bound borohydride 、 resin-bound periodate 、 氨 作用下， 以 甲醇 为溶剂， 反应 175.0h， 生成 1-[1-(1-benzoyloxymethyl-2-chloroethoxy)-2-chloroethyl]-3-tert-butoxycarbonylmethylthymine
  参考文献：
  名称：

  New Acyclonucleosides: Synthesis and Anti-HIV Activity

  摘要：

  The synthesis of new acyclic nucleosides is described. These syntheses were accomplished by various methods: glycosylation, selective or total deprotection, oxidation/reduction, chlorination or azidation of hydroxyl groups. The compounds were characterized with NMR, mass and IR spectroscopy. Antiviral properties of these compounds were evaluated on HIV-1 infected cell lines.

  DOI：

  10.1081/ncn-200067423
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 四氯化锡 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-tert-butoxycarbonylmethylthymine
  参考文献：
  名称：

  New Acyclonucleosides: Synthesis and Anti-HIV Activity

  摘要：

  The synthesis of new acyclic nucleosides is described. These syntheses were accomplished by various methods: glycosylation, selective or total deprotection, oxidation/reduction, chlorination or azidation of hydroxyl groups. The compounds were characterized with NMR, mass and IR spectroscopy. Antiviral properties of these compounds were evaluated on HIV-1 infected cell lines.

  DOI：

  10.1081/ncn-200067423

文献信息

• Selective Deprotection of Fully Benzoylated Nucleoside Derivatives
  作者：Rachida Zerrouki、Vincent Roy、Amel Hadj‐Bouazza、Pierre Krausz

  DOI：10.1081/car-200030095

  日期：2004.12.27

  Selective deprotection of benzoylated hydroxyl groups is one of the crucial problems in the synthesis of nucleoside analogues as well as of other polyfunctional molecules.

  苯甲酰化羟基的选择性脱保护是核苷类似物以及其他多官能分子合成中的关键问题之一。
• New Acyclonucleosides: Synthesis and Anti-HIV Activity
  作者：Amel Hadj-Bouazza、Rachida Zerrouki、Pierre Krausz、Géraldine Laumond、Anne Marie Aubertin、Yves Champavier

  DOI：10.1081/ncn-200067423

  日期：2005.7.1

  The synthesis of new acyclic nucleosides is described. These syntheses were accomplished by various methods: glycosylation, selective or total deprotection, oxidation/reduction, chlorination or azidation of hydroxyl groups. The compounds were characterized with NMR, mass and IR spectroscopy. Antiviral properties of these compounds were evaluated on HIV-1 infected cell lines.