(3S,4R,5S,6R)-3-hydroxymethyl-4,5,6-trihydroxyazepane hydrochloride | 1357281-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (3S,4R,5S,6R)-3-hydroxymethyl-4,5,6-trihydroxyazepane hydrochloride
• 英文别名: (3R,4S,5R,6S)-6-(hydroxymethyl)azepane-3,4,5-triol;hydrochloride
• CAS: 1357281-15-2
• 化学式: C₇H₁₅NO₄*ClH
• 分子量: 213.661
• InChiKey: JGGIEGNUHYBCIJ-LJTMIZJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3S,4R,5S,6R)-N-benzyloxycarbonyl-3-hydroxymethyl-4,5,6-tribenzyloxyazepane 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到(3S,4R,5S,6R)-3-hydroxymethyl-4,5,6-trihydroxyazepane hydrochloride
  参考文献：
  名称：

  Towards a stable noeuromycin analog with a d-manno configuration: Synthesis and glycosidase inhibition of d-manno-like tri- and tetrahydroxylated azepanes

  摘要：

  Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable D-gluco-like analogs have been reported, no data are available for D-manno-like structures. A series of tri- and tetrahydroxylated seven-membered iminosugars displaying either a D-manno-or a L-gulo-like configuration, were synthesized from methyl alpha-D-mannopyranoside using a reductive amination-mediated ring expansion as the key step. Screening towards a range of commercial glycosidases demonstrated their potency as competitive glycosidase inhibitors while cellular assay showed selective albeit weak glycoprotein processing mannosidase inactivation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.053

文献信息

• Towards a stable noeuromycin analog with a d-manno configuration: Synthesis and glycosidase inhibition of d-manno-like tri- and tetrahydroxylated azepanes
  作者：Julia Deschamp、Martine Mondon、Shinpei Nakagawa、Atsushi Kato、Dominic S. Alonzi、Terry D. Butters、Yongmin Zhang、Matthieu Sollogoub、Yves Blériot

  DOI：10.1016/j.bmc.2010.09.053

  日期：2012.1

  Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable D-gluco-like analogs have been reported, no data are available for D-manno-like structures. A series of tri- and tetrahydroxylated seven-membered iminosugars displaying either a D-manno-or a L-gulo-like configuration, were synthesized from methyl alpha-D-mannopyranoside using a reductive amination-mediated ring expansion as the key step. Screening towards a range of commercial glycosidases demonstrated their potency as competitive glycosidase inhibitors while cellular assay showed selective albeit weak glycoprotein processing mannosidase inactivation. (C) 2010 Elsevier Ltd. All rights reserved.