((2R,3R,4R,5S)-3-(benzoyloxy)-4-((methylsulfonyl)oxy)tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate | 1188366-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,4R,5S)-3-(benzoyloxy)-4-((methylsulfonyl)oxy)tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate
• CAS: 1188366-59-7
• 化学式: C₂₈H₂₆O₁₀S
• 分子量: 554.574
• InChiKey: XFWHKALAYHCLEJ-ZFFYZDHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  苯甲酰腈 、 2,5-anhydro-4-O-benzoyl-3,6-di-O-methanesulfonyl-D-glucitol 、 氰化四丁基铵 以 乙腈 为溶剂， 反应 76.0h， 以23%的产率得到3,6:4,5-dianhydro-7-O-benzoyl-2-deoxy-L-aloheptononitrile
  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