N-benzyl 1,2'-anhydro-5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-ribonamide | 1139832-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl 1,2'-anhydro-5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-ribonamide
• 英文别名: (4R,8R)-8-[(1R)-2-azido-1-hydroxyethyl]-2-benzyl-6,6-dimethyl-5,7-dioxa-2-azaspiro[3.4]octan-3-one
• CAS: 1139832-41-9
• 化学式: C₁₆H₂₀N₄O₄
• 分子量: 332.359
• InChiKey: CAKUEVDYCJMWCR-XJKCOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-benzyl 5-azido-5-deoxy-2-C-hydroxymethyl-2,3-isopropylidene-2'-O-trifluoromethanesulfonyl-D-ribonamide 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到N-benzyl 1,2'-anhydro-5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-ribonamide
  参考文献：
  名称：

  Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

  摘要：

  The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by all efficient intramolecular displacement of a highly hindered neopentyl triflate allows access to enantiopure THF derivatives which have carbon substituents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.012

文献信息

• Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds
  作者：Michela I. Simone、Alison A. Edwards、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.12.012

  日期：2008.12

  The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by all efficient intramolecular displacement of a highly hindered neopentyl triflate allows access to enantiopure THF derivatives which have carbon substituents. (C) 2008 Elsevier Ltd. All rights reserved.