(2S,3R,4S)-4-Azido-3-hydroxy-tetrahydro-furan-2-carboxylic acid | 909723-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,3R,4S)-4-Azido-3-hydroxy-tetrahydro-furan-2-carboxylic acid
• 英文别名: (2S,3R,4S)-4-azido-3-hydroxyoxolane-2-carboxylic acid
• CAS: 909723-68-8
• 化学式: C₅H₇N₃O₄
• 分子量: 173.128
• InChiKey: RYKVTECJWYZSRT-NUNKFHFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  115.52
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-4-Azido-3-hydroxy-tetrahydro-furan-2-carboxylic acid 在 palladium on activated charcoal 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 35.0h， 生成 (2S,3R,4S)-4-[((2S,3R,4S)-4-Amino-3-hydroxy-tetrahydro-furan-2-carbonyl)-amino]-3-hydroxy-tetrahydro-furan-2-carboxylic acid isopropyl ester
  参考文献：
  名称：

  A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry

  摘要：

  Two tetrahydrofuran-based y-amino acids [2,4-cis and 2,4-trans] were subjected to iterative peptide-coupling procedures to afford dimeric, tetrameric and hexameric carbopeptoids in good yield. These homooligomers were prepared for secondary structural study-to ascertain the conformational preference inherent in the monomer units. The L-xylo oligomers were protected with triethylsilyl ethers to increase the range of solvents suitable for structural investigation. Initial secondary structure data indicate the presence of hydrogen-bonded conformations in the L-ribo series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.067
• 作为产物：
  描述：

  methyl 2,5-anhydro-4-azido-4-deoxy-L-xylonate 在 氢氧化钾 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 (2S,3R,4S)-4-Azido-3-hydroxy-tetrahydro-furan-2-carboxylic acid
  参考文献：
  名称：

  A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry

  摘要：

  Two tetrahydrofuran-based y-amino acids [2,4-cis and 2,4-trans] were subjected to iterative peptide-coupling procedures to afford dimeric, tetrameric and hexameric carbopeptoids in good yield. These homooligomers were prepared for secondary structural study-to ascertain the conformational preference inherent in the monomer units. The L-xylo oligomers were protected with triethylsilyl ethers to increase the range of solvents suitable for structural investigation. Initial secondary structure data indicate the presence of hydrogen-bonded conformations in the L-ribo series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.067