(2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester | 848909-02-4

• 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: (2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester
• CAS: 848909-02-4
• 化学式: C₃₆H₃₈N₄O₆
• 分子量: 622.721
• InChiKey: NOYBSFUHUOFCGV-IVFJIKSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  126.22
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以100%的产率得到(2S,3R,4R,5S,6R)-5-Amino-2-hydroxymethyl-azepane-3,4,6-triol
  参考文献：
  名称：

  New 1-amino-1-deoxy- and 2-amino-2-deoxy-polyhydroxyazepanes: synthesis and inhibition of glycosidases

  摘要：

  Eight new seven-membered ring iminoalditols, displaying an amino group and a hydroxymethyl group on the ring, have been synthesized from D-arabinose via epoxidation of a protected azacycloheptene and subsequent nucleophilic opening. Three of them show a potent glycosidase inhibition on amyloglucosidase and, to a lesser extend, on alpha-L-fucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.005
• 作为产物：
  描述：

  (2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane 在 sodium azide 、 ammonium chloride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  New 1-amino-1-deoxy- and 2-amino-2-deoxy-polyhydroxyazepanes: synthesis and inhibition of glycosidases

  摘要：

  Eight new seven-membered ring iminoalditols, displaying an amino group and a hydroxymethyl group on the ring, have been synthesized from D-arabinose via epoxidation of a protected azacycloheptene and subsequent nucleophilic opening. Three of them show a potent glycosidase inhibition on amyloglucosidase and, to a lesser extend, on alpha-L-fucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.005

文献信息

• Design and synthesis of acetamido tri- and tetra-hydroxyazepanes: Potent and selective β-N-acetylhexosaminidase inhibitors
  作者：Hongqing Li、Filipa Marcelo、Claudia Bello、Pierre Vogel、Terry D. Butters、Amélia P. Rauter、Yongmin Zhang、Matthieu Sollogoub、Yves Blériot

  DOI：10.1016/j.bmc.2009.06.022

  日期：2009.8

  A series of seven-membered iminosugars bearing an acetamido group beta- or gamma- to the endocyclic nitrogen have been synthesized via simple transformations of previously described polysubstituted azepanes. These tetra- and trihydroxylated acetamido azepanes are ring homologues of 2-acetamido-1,2-dideoxy-glyconojirimycins and 2-acetamido-1-N-iminosugars respectively. Screening of these azepanes towards a range of commercially available glycosidases demonstrated their potential as selective and potent hexosaminidase inhibitors with K-i's in the submicromolar range. A correlation between the relative configuration of the azepanes and their ability to inactivate hexosaminidases was also observed for the first time for this class of compounds with one notable exception for the most potent compound. (C) 2009 Elsevier Ltd. All rights reserved.