(5R,6R,7R,8R)-5,6,7,8-tetrahydroxy-6,7-O-methylethylidene-2-imino-1,3-diazonane | 206655-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5R,6R,7R,8R)-5,6,7,8-tetrahydroxy-6,7-O-methylethylidene-2-imino-1,3-diazonane
• CAS: 206655-87-0
• 化学式: C₁₀H₁₉N₃O₄
• 分子量: 245.279
• InChiKey: CHIKUXGHISZNDW-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.64
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  106.83
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,6R,7R,8R)-5,6,7,8-tetrahydroxy-6,7-O-methylethylidene-2-imino-1,3-diazonane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以70%的产率得到(5R,6R,7R,8R)-5,6,7,8-tetrahydroxy-1,3-diazonan-2-iminium chloride
  参考文献：
  名称：

  Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases

  摘要：

  A series of enantiomerically pure C-2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N,N"-trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit alpha-L-fucosidase of bovin kidney (2.8 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00294-1
• 作为产物：
  描述：

  3,4-di-O-isopropylidene-D-mannitol 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氨 、 氢气 、 sodium 、 sodium hydride 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 (5R,6R,7R,8R)-5,6,7,8-tetrahydroxy-6,7-O-methylethylidene-2-imino-1,3-diazonane
  参考文献：
  名称：

  Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases

  摘要：

  A series of enantiomerically pure C-2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N,N"-trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit alpha-L-fucosidase of bovin kidney (2.8 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00294-1