N-(2-chloro-6-methylphenyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) trifluoroacetimidate | 1228757-64-9

• 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-(2-chloro-6-methylphenyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) trifluoroacetimidate
• CAS: 1228757-64-9
• 化学式: C₂₃H₂₅ClF₃NO₁₀
• 分子量: 567.9
• InChiKey: VHWQZFDVBRQPIE-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  136.02
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2-氯-6-甲基苯胺 在 四氯化碳 、 15-冠醚-5 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.58h， 生成 N-(2-chloro-6-methylphenyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) trifluoroacetimidate 、 N-(2-chloro-6-methylphenyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) trifluoroacetimidate
  参考文献：
  名称：

  N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors

  摘要：

  Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the -anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).

  DOI：

  10.1080/07328301003597673