Acetic acid (2S,3R,4R,5R)-5-aminomethyl-3,4-bis-benzyloxy-pyrrolidin-2-ylmethyl ester | 261951-31-9

• 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: Acetic acid (2S,3R,4R,5R)-5-aminomethyl-3,4-bis-benzyloxy-pyrrolidin-2-ylmethyl ester
• CAS: 261951-31-9
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: XUDRFBPFVZUVPG-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.81
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5R)-5-aminomethyl-3,4-bis-benzyloxy-pyrrolidin-2-ylmethyl ester 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-hydroxymethyl-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 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2S,3R,4R,5R)-5-aminomethyl-3,4-bis-benzyloxy-pyrrolidin-2-ylmethyl 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