methyl (4R,5R)-5-((R)-2-azido-1-hydroxyethyl)-2,2-dimethyl-4-((((trifluoromethyl)sulfonyl)oxy)methyl)-1,3-dioxolane-4-carboxylate | 1139832-37-3

• 英文名称: methyl (4R,5R)-5-((R)-2-azido-1-hydroxyethyl)-2,2-dimethyl-4-((((trifluoromethyl)sulfonyl)oxy)methyl)-1,3-dioxolane-4-carboxylate
• CAS: 1139832-37-3
• 化学式: C₁₁H₁₆F₃N₃O₈S
• 分子量: 407.325
• InChiKey: PRFJCTWDIDRTJA-BRDIYROLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  157.12
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-2'-C-trifluoromethanesulfonyl-D-ribono-1,4-lactone 、 sodium methylate 以 甲醇 为溶剂， 生成 methyl (4R,5R)-5-((R)-2-azido-1-hydroxyethyl)-2,2-dimethyl-4-((((trifluoromethyl)sulfonyl)oxy)methyl)-1,3-dioxolane-4-carboxylate
  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