N-benzyl-β-D-mannopyranosylamine | 70428-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-β-D-mannopyranosylamine
• 英文别名: (2R,3S,4S,5S,6R)-2-(benzylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 70428-27-2
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: JMAHBQWKTCJRGQ-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyl-β-D-mannopyranosylamine 以 水 为溶剂， 反应 3.0h， 生成 1-benzyl-4-((1S,2R,3S)-1,2,3,4-tetrahydroxybutyl)-1,3-dihydro-2H-imidazole-2-thione
  参考文献：
  名称：

  A bioinspired look at the glucosinolate metabolic pathway. Structural insights into the reaction of benzyl isothiocyanate and d-glucosamine

  摘要：

  Through a well-established enzymatic transformation glucosinolates release reactive isothiocyanates that can undergo further metabolic pathways affording a plethora of reactive metabolites. This study explores in detail the reaction of benzyl isothiocyanate, which possesses antitumor activity as alkylating agent, with D-glucosamine, commonly employed in oral treatments against osteoarthritis and inflammation. Structures of the resulting products and their evolution have been assessed and compared with those involving D-glucose, reported previously. Chemical results suggest that clinical treatments with o-glucosamine could reduce the beneficial effects associated with diets based on glucosinolate-rich foods. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.073
• 作为产物：
  描述：

  D-mannose 、 苄胺 以 乙醇 为溶剂， 反应 0.08h， 以58%的产率得到N-benzyl-β-D-mannopyranosylamine
  参考文献：
  名称：

  Synthesis of N-substituted D-mannosylamines and 1-(benzylamino)-1-deoxy-alditols for biological evaluation

  摘要：

  DOI：

  10.1016/s0008-6215(00)85528-7

文献信息

• Synthesis of N-substituted D-mannosylamines and 1-(benzylamino)-1-deoxy-alditols for biological evaluation
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、T.Y. Shen

  DOI：10.1016/s0008-6215(00)85528-7

  日期：1980.6
• A bioinspired look at the glucosinolate metabolic pathway. Structural insights into the reaction of benzyl isothiocyanate and d-glucosamine
  作者：Guadalupe Silvero、Martín Ávalos、Reyes Babiano、Pedro Cintas、José L. Jiménez、Juan C. Palacios

  DOI：10.1016/j.tet.2011.07.073

  日期：2011.10

  Through a well-established enzymatic transformation glucosinolates release reactive isothiocyanates that can undergo further metabolic pathways affording a plethora of reactive metabolites. This study explores in detail the reaction of benzyl isothiocyanate, which possesses antitumor activity as alkylating agent, with D-glucosamine, commonly employed in oral treatments against osteoarthritis and inflammation. Structures of the resulting products and their evolution have been assessed and compared with those involving D-glucose, reported previously. Chemical results suggest that clinical treatments with o-glucosamine could reduce the beneficial effects associated with diets based on glucosinolate-rich foods. (C) 2011 Elsevier Ltd. All rights reserved.