3,4,5,7-tetra-O-benzoyl-2-deoxy-2-propanamido-α-D-gluco-hept-2-ulopyranosononitrile | 1337568-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,7-tetra-O-benzoyl-2-deoxy-2-propanamido-α-D-gluco-hept-2-ulopyranosononitrile
• 英文别名: N-propanoyl-2,3,4,6-tetra-O-benzoyl-1-cyano-α-D-glucopyranosylamine
• CAS: 1337568-56-5
• 化学式: C₃₈H₃₂N₂O₁₀
• 分子量: 676.679
• InChiKey: OPPDKJWSDHSOOP-YJODGFBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  167.32
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  丙腈 、 (2R,3R,4S,5R)-6-[(苯甲酰氧基)甲基]-2-溴-2-氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 silver carbonate 作用下， 反应 48.0h， 以57%的产率得到3,4,5,7-tetra-O-benzoyl-2-deoxy-2-propanamido-α-D-gluco-hept-2-ulopyranosononitrile
  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