[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phenylmethoxymethyl)oxolan-3-yl] benzoate | 175230-18-9

• 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: [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phenylmethoxymethyl)oxolan-3-yl] benzoate
• CAS: 175230-18-9
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: MKRKUBJSWPKEHT-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(2R,3S)-5-methoxy-2-(phenylmethoxymethyl)oxolan-3-yl] benzoate 、 O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phenylmethoxymethyl)oxolan-3-yl] benzoate 、 (2R,3S,5S)-2-((benzyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group

  摘要：

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.006

文献信息

• Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group
  作者：Zhaogui Liu、Deyao Li、Biaolin Yin、Jiancun Zhang

  DOI：10.1016/j.tetlet.2009.09.006

  日期：2010.1

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.