2,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-D-mannitol | 206655-92-7

• 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: 2,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-D-mannitol
• 英文别名: (4R,5R)-4,5-bis[(1R)-1-azido-2-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 206655-92-7
• 化学式: C₂₃H₂₈N₆O₄
• 分子量: 452.513
• InChiKey: ZUALHLNDGGFBEX-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-D-mannitol 在 palladium on activated charcoal 氢气 、 sodium 、 三乙胺 作用下， 以 二氯甲烷 、 氨 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Synthesis of C2-symmetric bis(cyclic isothioureas) as potent inhibitors of glycosidases

  摘要：

  Enantiopure C-2-symmetric bis(cyclic isothioureas), considered as potent inhibitors of glycosidases, have been synthesized from D-mannitol. The key step involved a mercuric-catalyzed transformation of a cyclic 1,3-thiazolidine-2-thione into a 2-N-tert-butylamino-1,3-thiazoline. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00593-6
• 作为产物：
  描述：

  3,4-O-methylethylidene-D-mannitol 在 sodium azide 、 四丁基碘化铵 、 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 2,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-D-mannitol
  参考文献：
  名称：

  Synthesis of C2-symmetric bis(cyclic isothioureas) as potent inhibitors of glycosidases

  摘要：

  Enantiopure C-2-symmetric bis(cyclic isothioureas), considered as potent inhibitors of glycosidases, have been synthesized from D-mannitol. The key step involved a mercuric-catalyzed transformation of a cyclic 1,3-thiazolidine-2-thione into a 2-N-tert-butylamino-1,3-thiazoline. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00593-6

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。
• Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases
  作者：Yves Le Merrer、Laurence Gauzy、Christine Gravier-Pelletier、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00294-1

  日期：2000.2

  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.