2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-gluconothioamide | 948040-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-gluconothioamide
• 英文别名: [(2R,3R,4S,5R)-3-benzoyloxy-5-carbamothioyl-4-methylsulfonyloxyoxolan-2-yl]methyl benzoate
• CAS: 948040-42-4
• 化学式: C₂₁H₂₁NO₈S₂
• 分子量: 479.532
• InChiKey: CHOYQZHAUTWVHR-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-gluconothioamide 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 192.83h， 生成 2-(2,3-anhydro-β-D-ribofuranosyl)thiazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring

  摘要：

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-P-Dribofuranosyl)thiazole-4-carboxamide (2',3'anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides, as well as evaluation of their antitumour activities in vitro. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.050
• 作为产物：
  描述：

  2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 、 盐酸 、 硫化氢 、 盐酸羟胺 、 sodium acetate 、 甲基磺酰氯 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 170.5h， 生成 2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-gluconothioamide
  参考文献：
  名称：

  Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring

  摘要：

  This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-P-Dribofuranosyl)thiazole-4-carboxamide (2',3'anhydro-tiazofurin) and the corresponding alpha- and beta-homo-C-nucleosides, as well as evaluation of their antitumour activities in vitro. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.050

文献信息

• Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring
  作者：Mirjana Popsavin、Saša Spaić、Miloš Svirčev、Vesna Kojić、Gordana Bogdanović、Vjera Pejanović、Velimir Popsavin

  DOI：10.1016/j.tet.2009.06.100

  日期：2009.9

  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