N-acetyl-2,3,4,6-tetra-O-acetyl-1-cyano-β-D-galactopyranosylamine | 1337568-53-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-2,3,4,6-tetra-O-acetyl-1-cyano-β-D-galactopyranosylamine
• 英文别名: 2-acetamido-3,4,5,7-tetra-O-acetyl-2-deoxy-β-D-galacto-hept-2-ulopyranosononitrile；[(2R,3S,4S,5R,6R)-6-acetamido-3,4,5-triacetyloxy-6-cyanooxan-2-yl]methyl acetate
• CAS: 1337568-53-2
• 化学式: C₁₇H₂₂N₂O₁₀
• 分子量: 414.369
• InChiKey: MNXVEXOOAQIMJY-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  乙腈 、 (2R,3R,4S,5S)-6-(乙酰氧基甲基)-2-溴-2-氨基甲酰四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 氯化铟 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 生成 N-acetyl-2,3,4,6-tetra-O-acetyl-1-cyano-β-D-galactopyranosylamine 、 N-acetyl-2,3,4,6-tetra-O-acetyl-1-cyano-α-D-galactopyranosylamine
  参考文献：
  名称：

  Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

  摘要：

  O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-D-glycopyranosyl)formamides of D-gluco, D-galacto, and D-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-D-glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr2, Hg(CN)(2), or InCl3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH3NO2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-beta-D-galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric alpha-amino acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.001