1,6-diamino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-D-mannitol | 180589-06-4

• 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: 1,6-diamino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-D-mannitol
• CAS: 180589-06-4
• 化学式: C₂₃H₃₂N₂O₄
• 分子量: 400.518
• InChiKey: SRQDWVUANGZBFY-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,6-diamino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-D-mannitol 在 盐酸 、 氨 、 sodium 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (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 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1,6-diamino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-D-mannitol
  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

文献信息

• Synthesis of C₂-Symmetrical Cyclic Guanidino-Sugars from d-Mannitol
  作者：Laurence Gauzy、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1055/s-1998-3129

  日期：1998.4

  An efficient method für the synthesis of C2-symmetrical cyclic guanidino-sugars has been developed from 1,2:5,6-dianhydro-3,4-O-methylethylidene-d-mannitol or l-iditol.

  从 1,2:5,6-二氢-3,4-O-甲基亚乙基-d-甘露醇或 l-iditol 中开发出了一种合成 C2 对称环状胍基糖的高效方法。