(3aS,5S,6R,6aR)-3-benzyl-5-((R)-1,2-dihydroxyethyl)-6-hydroxyhexahydro-2H-furo[2,3-d]imidazole-2-thione | 1338454-88-8

• 分子结构分类: 有机化合物
• 英文名称: (3aS,5S,6R,6aR)-3-benzyl-5-((R)-1,2-dihydroxyethyl)-6-hydroxyhexahydro-2H-furo[2,3-d]imidazole-2-thione
• CAS: 1338454-88-8
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: MALGHCIDMXQOKE-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.19
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aS,5S,6R,6aR)-3-benzyl-5-((R)-1,2-dihydroxyethyl)-6-hydroxyhexahydro-2H-furo[2,3-d]imidazole-2-thione 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以75%的产率得到C₂₀H₂₄N₂O₇S
  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-glucosamine hydrochloride 在 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 (3aS,5S,6R,6aR)-3-benzyl-5-((R)-1,2-dihydroxyethyl)-6-hydroxyhexahydro-2H-furo[2,3-d]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