(3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one | 1328893-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one
• CAS: 1328893-60-2
• 化学式: C₂₀H₂₃N₃O₁₁
• 分子量: 481.416
• InChiKey: VKINVDQATGIVKK-SGWZHLPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  161.97
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1,2; 5,6-di-O-isopropylidene-3-C-[[[(phenylmethoxy)carbonyl]amino]methyl]-α-D-allofuranose 在 1,2; 5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.92h， 生成 (3R)-3'-(2,4-dinitrophenyl)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one
  参考文献：
  名称：

  A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate

  摘要：

  A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.04.008