1-O-acetyl-6-N-acetylamino-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-D-glucitol | 261951-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-acetyl-6-N-acetylamino-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-D-glucitol
• CAS: 261951-34-2
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: NTTSUHHGXJKBQS-UEQSERJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.89
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-6-N-acetylamino-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-D-glucitol 在 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of d-glucose with 6-amino-6-deoxy-2,5-imino-d-glucitol

  摘要：

  Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C-2 symmetric bis-aziridine deriving from D-mannitol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00817-x
• 作为产物：
  描述：

  1-O-acetyl-3,4-di-O-benzyl-6-[(tert-butyloxycarbonyl)amino]-2,5-[(tert-butyloxycarbonyl)imino]-2,5,6-trideoxy-D-glucitol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-O-acetyl-6-N-acetylamino-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-D-glucitol
  参考文献：
  名称：

  Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives

  摘要：

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00267-9