dibenzyl [(R)-hydroxy[(2S,3S,4R,5R,6R)-3,4,6-tris(benzyloxy)-5-(dibenzylamino)tetrahydro-2H-pyran-2-yl]methyl]phosphonate | 1404058-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl [(R)-hydroxy[(2S,3S,4R,5R,6R)-3,4,6-tris(benzyloxy)-5-(dibenzylamino)tetrahydro-2H-pyran-2-yl]methyl]phosphonate
• CAS: 1404058-87-2
• 化学式: C₅₅H₅₆NO₈P
• 分子量: 890.025
• InChiKey: NJTIMQZUYMFFKW-HPYZEWSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.11
• 重原子数：
  65.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  dibenzyl [(R)-hydroxy[(2S,3S,4R,5R,6R)-3,4,6-tris(benzyloxy)-5-(dibenzylamino)tetrahydro-2H-pyran-2-yl]methyl]phosphonate 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(S)-((R)-(bis(benzyloxy)phosphoryl)((2S,3S,4R,5R,6R)-3,4,6-tris(benzyloxy)-5-(dibenzylamino)tetrahydro-2H-pyran-2-yl)methyl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Synthesis and evaluation of glucosamine-6-phosphate analogues as activators of glmS riboswitch

  摘要：

  The glmS riboswitch is a ribozyme found in numerous Gram-positive bacteria and responds to the cellular concentrations of glucosamine 6-phosphate (GlcN6P). Given the importance of GlcN6P for cell wall biosynthesis, the glmS riboswitch has become a new drug target for the development of antibiotics. Herein, we describe the efficient synthesis of three GlcN6P analogues and their evaluation on inducing self-cleavage of the glmS riboswitch from Bacillus subtilis. Our results provide valuable information for further elucidation of the structure activity relationships and drug design for glmS riboswitch antibiotics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.015
• 作为产物：
  描述：

  2-deoxy-2-amino glucose 在 甲醇 、 硫酸 、 sodium methylate 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 32.0h， 生成 dibenzyl [(R)-hydroxy[(2S,3S,4R,5R,6R)-3,4,6-tris(benzyloxy)-5-(dibenzylamino)tetrahydro-2H-pyran-2-yl]methyl]phosphonate
  参考文献：
  名称：

  Synthesis and evaluation of glucosamine-6-phosphate analogues as activators of glmS riboswitch

  摘要：

  The glmS riboswitch is a ribozyme found in numerous Gram-positive bacteria and responds to the cellular concentrations of glucosamine 6-phosphate (GlcN6P). Given the importance of GlcN6P for cell wall biosynthesis, the glmS riboswitch has become a new drug target for the development of antibiotics. Herein, we describe the efficient synthesis of three GlcN6P analogues and their evaluation on inducing self-cleavage of the glmS riboswitch from Bacillus subtilis. Our results provide valuable information for further elucidation of the structure activity relationships and drug design for glmS riboswitch antibiotics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.015