methyl (2S,3S,4R,6R)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylate | 1033110-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,4R,6R)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylate
• CAS: 1033110-15-4
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: USFWUHCYZZEXPS-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4R,6R)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到(2S,3S,4R,6R)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylic 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-β-D-arabinohexopyranosid)uronate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到methyl (2S,3S,4R,6R)-4-amino-3-hydroxy-6-methoxyoxane-2-carboxylate
  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