1,3-di-O-benzyl-2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol | 221112-18-1

• 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: 1,3-di-O-benzyl-2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol
• 英文别名: 2-[1,3-bis(phenylmethoxy)propan-2-ylamino]ethanol
• CAS: 221112-18-1
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: HUBQQTCEWQFNST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以33%的产率得到2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol
  参考文献：
  名称：

  Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors

  摘要：

  The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displacement of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 and 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). The inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00031-9
• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 1,3-di-O-benzyl-2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol
  参考文献：
  名称：

  Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors

  摘要：

  The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displacement of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 and 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). The inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00031-9

文献信息

• Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors
  作者：El Sayed H. El Ashry、Adel A.-H. Abdel-Rahman、Yeldez El Kilany、Richard R. Schmidt

  DOI：10.1016/s0040-4020(99)00031-9

  日期：1999.2

  The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displacement of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 and 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). The inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.