(2R,3S)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran-3-yl ((benzyloxy)carbonyl)glycinate | 1207737-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran-3-yl ((benzyloxy)carbonyl)glycinate
• CAS: 1207737-87-8
• 化学式: C₂₃H₂₇NO₇
• 分子量: 429.47
• InChiKey: FGLORHICHKMUKI-RJKSWSIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran-3-yl ((benzyloxy)carbonyl)glycinate 、 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)-2-((benzyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl ((benzyloxy)carbonyl)glycinate 、
  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