1-[(2R,3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-hydroxyoxolan-2-yl]pyrimidine-2,4-dione | 1446785-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-hydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1446785-73-4
• 化学式: C₂₄H₂₈N₂O₅Si
• 分子量: 452.582
• InChiKey: NYIXNFMCLBSXBO-ILWGZMRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1′α-(uracil-1-yl)-2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-L-threose 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 1-[(2R,3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-hydroxyoxolan-2-yl]pyrimidine-2,4-dione 、 1-((2R,3S,4S)-3-((tert-butyldiphenylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of α-l-Threose Nucleoside Phosphonates via Regioselective Sugar Protection

  摘要：

  A new synthesis route to a-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.

  DOI：

  10.1021/jo400907g

文献信息

• Synthesis of α-<scp>l</scp>-Threose Nucleoside Phosphonates via Regioselective Sugar Protection
  作者：Shrinivas G. Dumbre、Mi-Yeon Jang、Piet Herdewijn

  DOI：10.1021/jo400907g

  日期：2013.7.19

  A new synthesis route to a-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.