methyl (2S,3S,4R,6R)-3-acetyloxy-4-azido-6-methoxyoxane-2-carboxylate | 1012795-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl (2S,3S,4R,6R)-3-acetyloxy-4-azido-6-methoxyoxane-2-carboxylate
• CAS: 1012795-20-8
• 化学式: C₁₀H₁₅N₃O₆
• 分子量: 273.246
• InChiKey: LZTKGYVZXPTGAS-HXFLIBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4R,6R)-3-acetyloxy-4-azido-6-methoxyoxane-2-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以71%的产率得到methyl (methyl 3-azido-2,3-dideoxy-β-D-arabinohexopyranosid)uronate
  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：

  甲醇 、 在 2,4,6-三甲基吡啶 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以39%的产率得到methyl (2S,3S,4R,6R)-3-acetyloxy-4-azido-6-methoxyoxane-2-carboxylate
  参考文献：
  名称：

  Synthesis and geometry of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-α/β-d-arabino- and -α/β-d-ribo-hexopyranosid)uronates

  摘要：

  The synthesis of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-alpha/beta-D-arabino- and -(alpha/beta-D-ribo-hexopyranosid)uronates is presented. High resolution H-1 and C-13 NMR spectral data for all diastereoisomers and single-crystal X-ray diffraction analysis for methyl (methyl 3-azido-2,3-dideoxy-beta-D-arabino-hexopyranosid)uronate are reported. The planarity of the 4-OAc and 5-COOMe groups as well as the orientations of the aglycone and azide groups in the crystal lattice is discussed. The influence of the 5-COOMe group on the pyranose ring conformation is considered. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.001