1,6-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-L-iditol | 914982-52-8

• 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-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-L-iditol
• CAS: 914982-52-8
• 化学式: C₂₅H₃₄O₁₀S₂
• 分子量: 558.671
• InChiKey: UTZLCXCRCJJJBT-CJRSTVEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,6-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-L-iditol 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium 作用下， 以 氨 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 {(R)-1-[(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester
  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 四丁基碘化铵 、 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 1,6-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-L-iditol
  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.