2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl cyanide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl cyanide
• 英文别名: 2,3,4,6-tetra-O-benzoyl-b-D-glucopyranosylcyanide；[(2R,3R,4R,5S,6R)-3,4,5-tribenzoyloxy-6-cyanooxan-2-yl]methyl benzoate
• 化学式: C₃₅H₂₇NO₉
• 分子量: 605.601
• InChiKey: JKHRAWZFZMGIKG-PXPWAULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  138.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl cyanide 在 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 16.0h， 生成 5-(2'-deoxy-d-arabino-hex-1'-enopyranosyl)-3-(2-naphthyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  C-(2-Deoxy-d-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors

  摘要：

  Synthetic methods were elaborated for D-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-D-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplen debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.04.016
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 氰化汞 以 硝基甲烷 为溶剂， 反应 48.0h， 以56%的产率得到(2R,3R,4R,5S,6S)-2-[(苯甲酰氧基)甲基]-6-氰基四氢-2H-吡喃-3,4,5-三基三苯甲酸酯
  参考文献：
  名称：

  一种新的可扩展制备的吡喃葡萄糖亚基-螺硫代乙内酰脲：糖原磷酸化酶的最佳抑制剂之一

  摘要：

  在硝基甲烷中，氰化汞（II）将苯溴-葡萄糖转化为过邻苯甲酰化的β-d-吡喃葡萄糖基氰化物。用溴化氢在乙酸中腈的部分水解得到过-O-苯甲酰化的C-（β-d-吡喃葡萄糖基）甲酰胺。使用溴在四氯化碳，氯仿或二氯甲烷中进行光溴化，得到相应的过-O-苯甲酰化的1-溴-1-脱氧-β-d-吡喃葡萄糖基氰化物和C-（1-溴-1-脱氧-β-d-吡喃葡萄糖基）甲酰胺 后者与硫氰酸铵在硝基甲烷中的反应得到过-O-苯甲酰化的C- 6S构型的吡喃吡喃基亚烷基-螺-硫代乙内酰脲，以及少量的O-苯甲酰化的C-（1-羟基-β-d-吡喃葡萄糖基）甲酰胺。在甲醇中用甲醇钠对螺硫代乙内酰脲进行脱苯甲酰化，得到克量的标题抑制剂。所描述的序列应适合于按比例放大，并且可以从d-葡萄糖开始以约30％的总收率制备目标化合物。

  DOI：

  10.1016/s0957-4166(00)00107-5

文献信息

• A new, scalable preparation of a glucopyranosylidene-spiro-thiohydantoin: one of the best inhibitors of glycogen phosphorylases
  作者：László Somsák、Veronika Nagy

  DOI：10.1016/s0957-4166(00)00107-5

  日期：2000.5

  per-O-benzoylated β-d-glucopyranosyl cyanide by mercury(II) cyanide in nitromethane. Partial hydrolysis of the nitrile with hydrogen bromide in acetic acid gave per-O-benzoylated C-(β-d-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-β-d-glucopyranosyl cyanide and C-(1-bromo-1-deoxy-β-d-

  在硝基甲烷中，氰化汞（II）将苯溴-葡萄糖转化为过邻苯甲酰化的β-d-吡喃葡萄糖基氰化物。用溴化氢在乙酸中腈的部分水解得到过-O-苯甲酰化的C-（β-d-吡喃葡萄糖基）甲酰胺。使用溴在四氯化碳，氯仿或二氯甲烷中进行光溴化，得到相应的过-O-苯甲酰化的1-溴-1-脱氧-β-d-吡喃葡萄糖基氰化物和C-（1-溴-1-脱氧-β-d-吡喃葡萄糖基）甲酰胺 后者与硫氰酸铵在硝基甲烷中的反应得到过-O-苯甲酰化的C- 6S构型的吡喃吡喃基亚烷基-螺-硫代乙内酰脲，以及少量的O-苯甲酰化的C-（1-羟基-β-d-吡喃葡萄糖基）甲酰胺。在甲醇中用甲醇钠对螺硫代乙内酰脲进行脱苯甲酰化，得到克量的标题抑制剂。所描述的序列应适合于按比例放大，并且可以从d-葡萄糖开始以约30％的总收率制备目标化合物。
• C-(2-Deoxy-d-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors
  作者：Éva Bokor、Eszter Szennyes、Tibor Csupász、Nóra Tóth、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2015.04.016

  日期：2015.8

  Synthetic methods were elaborated for D-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-D-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplen debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b. (C) 2015 Elsevier Ltd. All rights reserved.