1,2,3,5,6-penta-O-benzyl-4-di-O-methanesulfonyl-D-glucitol | 784151-22-0

• 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: 1,2,3,5,6-penta-O-benzyl-4-di-O-methanesulfonyl-D-glucitol
• CAS: 784151-22-0
• 化学式: C₃₆H₄₂O₁₀S₂
• 分子量: 698.855
• InChiKey: MPQLSMPGUAEYPJ-IYKITFJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  48.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6-penta-O-benzyl-4-di-O-methanesulfonyl-D-glucitol 在 Wilkinson's catalyst potassium carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 27.0h， 生成 1'-((2,3,5,6-tetra-O-benzyl-1,4-dideoxy-1,4-imino-D-galactitol)-4-N-ammonium)-2',4'-O-benzylidene-1'-deoxy-L-erythritol-3'-sulfate
  参考文献：
  名称：

  Synthesis of novel ammonium and selenonium ions and their evaluation as inhibitors of UDP-galactopyranose mutase

  摘要：

  The syntheses of two ammonium salts of 1,4-dideoxy-1,4-imino-D-galactitol containing erythritol sulfate side chains are described. The parent compound is a known inhibitor of the enzyme UDP-galactopyranose mutase (UDP-galactopyranose furanomutase, E.C. 5.4.99.9), which is responsible for the conversion of UDP-galactopyranose into UDP-galactofuranose and is presumably protonated in its active form. The side chain was chosen because it is present in a known sulfonium ion alpha-glucosidase inhibitor, salacinol. The syntheses of the selenonium analogues derived from 1,4-dideoxy-1,4-seleno-D-galactitol are also described. The synthetic strategy in the syntheses of all four salts involved the nucleophilic attack of a protected derivative of the alditol at the least hindered carbon of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate to give adducts that were subsequently deprotected. The importance of different protecting groups used in the various syntheses is also highlighted. Enzyme inhibition assays carried out on these compounds, and the corresponding sulfonium ions synthesized previously, show that they are poor inhibitors of UDP-galactopyranose mutase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.012
• 作为产物：
  描述：

  甲基磺酰氯 、 (2S,3S,4R,5R)-2,3,5,6-tetrakis(phenylmethoxy)hexane-1,4-diol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到1,2,3,5,6-penta-O-benzyl-4-di-O-methanesulfonyl-D-glucitol
  参考文献：
  名称：

  Synthesis of novel ammonium and selenonium ions and their evaluation as inhibitors of UDP-galactopyranose mutase

  摘要：

  The syntheses of two ammonium salts of 1,4-dideoxy-1,4-imino-D-galactitol containing erythritol sulfate side chains are described. The parent compound is a known inhibitor of the enzyme UDP-galactopyranose mutase (UDP-galactopyranose furanomutase, E.C. 5.4.99.9), which is responsible for the conversion of UDP-galactopyranose into UDP-galactofuranose and is presumably protonated in its active form. The side chain was chosen because it is present in a known sulfonium ion alpha-glucosidase inhibitor, salacinol. The syntheses of the selenonium analogues derived from 1,4-dideoxy-1,4-seleno-D-galactitol are also described. The synthetic strategy in the syntheses of all four salts involved the nucleophilic attack of a protected derivative of the alditol at the least hindered carbon of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate to give adducts that were subsequently deprotected. The importance of different protecting groups used in the various syntheses is also highlighted. Enzyme inhibition assays carried out on these compounds, and the corresponding sulfonium ions synthesized previously, show that they are poor inhibitors of UDP-galactopyranose mutase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.012