methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid | 1033110-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid
• 英文别名: (2S,3S,4S,6S)-4-azido-3-hydroxy-6-methoxyoxane-2-carboxylic acid
• CAS: 1033110-00-7
• 化学式: C₇H₁₁N₃O₅
• 分子量: 217.181
• InChiKey: MPQZBVSAPORIQD-BXKVDMCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以76%的产率得到methyl 3-amino-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid
  参考文献：
  名称：

  Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides

  摘要：

  The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -alpha,beta-D-arabino-, -alpha,beta-D-ribo, and -alpha,beta-L-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of H-1 NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.018
• 作为产物：
  描述：

  methyl (methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosid)uronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranosiduronic acid
  参考文献：
  名称：

  Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides

  摘要：

  The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -alpha,beta-D-arabino-, -alpha,beta-D-ribo, and -alpha,beta-L-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of H-1 NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.018

文献信息

• Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides
  作者：Dorota Tuwalska、Joanna Sienkiewicz、Beata Liberek

  DOI：10.1016/j.carres.2008.02.018

  日期：2008.5

  The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -alpha,beta-D-arabino-, -alpha,beta-D-ribo, and -alpha,beta-L-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of H-1 NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported. (c) 2008 Elsevier Ltd. All rights reserved.