(3R,4R,5R,6R)-N-benzyloxycarbonyl-3-oxo-4,5,6-tribenzyloxyazepane | 1357281-01-6

• 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: (3R,4R,5R,6R)-N-benzyloxycarbonyl-3-oxo-4,5,6-tribenzyloxyazepane
• CAS: 1357281-01-6
• 化学式: C₃₅H₃₅NO₆
• 分子量: 565.666
• InChiKey: XGQHJWJWNKKBKT-CKOYEXALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,6R)-N-benzyloxycarbonyl-3-oxo-4,5,6-tribenzyloxyazepane 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以50%的产率得到(3R,4S,5R)-N-benzyloxycarbonyl-3-methylene-4,5,6-tribenzyloxyazepane
  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
• 作为产物：
  描述：

  methyl 6-O-tosyl-α-D-mannopyranoside 在 sodium azide 、 硫酸 、 palladium on activated charcoal 、 氢气 、 sodium methylate 、 sodium hydride 、 potassium hydrogencarbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.08h， 生成 (3R,4R,5R,6R)-N-benzyloxycarbonyl-3-oxo-4,5,6-tribenzyloxyazepane
  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