3,4-di-O-benzyl-2,5-[(6-oxycarbonyl)imino]-2,5-dideoxy-D-glucitol | 184017-44-5

• 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: 3,4-di-O-benzyl-2,5-[(6-oxycarbonyl)imino]-2,5-dideoxy-D-glucitol
• 英文别名: (5S,6R,7R,7aR)-5-(hydroxymethyl)-6,7-bis(phenylmethoxy)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 184017-44-5
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: STMQXBXMDIEPTC-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-2,5-[(6-oxycarbonyl)imino]-2,5-dideoxy-D-glucitol 在 钯 氢气 、 potassium carbonate 作用下， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  从C 2对称双氮丙啶制备D-甘露糖和D-葡萄糖氮杂糖的实用途径

  摘要：

  由构型柔性的N -Boc双氮丙啶合成了被游离羟基取代的6-氨基-2,5-亚氨基-D-葡萄糖醇2和6-氨基-1,5-亚氨基-D-甘露糖醇3 1。乙酸对1的区域选择性开环是朝向2的直接方法，而在三氟甲磺酸催化下1与水或烯丙醇的反应则选择性地产生了氮杂吡喃糖3。在环状氨基甲酸酯保护的吡咯烷4上进行的亚硝酸脱氨基反应生成2,5-亚氨基-D-葡萄糖醇5和6的1：1混合物 在C-1或C-6带有一个游离羟基取代基。

  DOI：

  10.1016/0040-4039(96)01732-7
• 作为产物：
  描述：

  (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 在 dilithium tetrabromonickelate(II) 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 3,4-di-O-benzyl-2,5-[(6-oxycarbonyl)imino]-2,5-dideoxy-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

文献信息

• Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives
  作者：Isabelle McCort、Sébastien Fort、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00267-9

  日期：2000.1

  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.
• Practical route to D-manno and D-gluco azasugars from C2 symmetric bis-aziridines
  作者：Isabelle McCort、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/0040-4039(96)01732-7

  日期：1996.10

  hydroxyl group, have been synthesized from the conformationally flexible N-Boc bis-aziridine 1. Regioselective ring-opening of 1 by acetic acid is a straight way towards 2, while reaction of 1 with water or allylic alcohol under ytterbium triflate catalysis produces selectively the azapyranose 3. Nitrous deamination carried out on the cyclic carbamate-protected pyrrolidine 4 leads to a 1:1 mixture of both

  由构型柔性的N -Boc双氮丙啶合成了被游离羟基取代的6-氨基-2,5-亚氨基-D-葡萄糖醇2和6-氨基-1,5-亚氨基-D-甘露糖醇3 1。乙酸对1的区域选择性开环是朝向2的直接方法，而在三氟甲磺酸催化下1与水或烯丙醇的反应则选择性地产生了氮杂吡喃糖3。在环状氨基甲酸酯保护的吡咯烷4上进行的亚硝酸脱氨基反应生成2,5-亚氨基-D-葡萄糖醇5和6的1：1混合物 在C-1或C-6带有一个游离羟基取代基。