2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucitol | 1188366-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucitol
• CAS: 1188366-55-3
• 化学式: C₁₅H₂₀O₁₀S₂
• 分子量: 424.45
• InChiKey: VJFNGCKFWNTBLI-REWJHTLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  142.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  苯甲酰腈 、 2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucitol 在 potassium cyanide 作用下， 以 二甲基亚砜 为溶剂， 以8%的产率得到
  参考文献：
  名称：

  Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring

  摘要：

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-beta-D-ribofuranosyl)thiazole-4-carboxamide (2',3'-anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides. The synthetic approach was based on a multistep transformation of D-glucose into suitably protected aldonthioamides followed by their subsequent cyclocondensation with ethyl bromopyruvate to form the thiazole ring. Antiproliferative activity of the target molecules is reported against several human tumour cell lines. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.06.100
• 作为产物：
  描述：

  (2R,3R,4S,5R)-5-formyl-4-((methylsulfonyl)oxy)-2-(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl benzoate 在 sodium tetrahydroborate 、 水 、 sodium chloride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以1.484 g的产率得到2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucitol
  参考文献：
  名称：

  Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring

  摘要：

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-beta-D-ribofuranosyl)thiazole-4-carboxamide (2',3'-anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides. The synthetic approach was based on a multistep transformation of D-glucose into suitably protected aldonthioamides followed by their subsequent cyclocondensation with ethyl bromopyruvate to form the thiazole ring. Antiproliferative activity of the target molecules is reported against several human tumour cell lines. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.06.100