3-bromo-3,4-dihydro-4-hydroxy-3,5-dinitro-2-[1,2:3,4-di-O-isopropyliden-β-L-arabinopyranosid-5-yl]-2H-1-benzopyran | 1509952-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-bromo-3,4-dihydro-4-hydroxy-3,5-dinitro-2-[1,2:3,4-di-O-isopropyliden-β-L-arabinopyranosid-5-yl]-2H-1-benzopyran
• CAS: 1509952-33-3
• 化学式: C₂₀H₂₃BrN₂O₁₁
• 分子量: 547.313
• InChiKey: XCBQRHPZSFYIII-LULZHNAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  161.89
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-bromo-3,4-dihydro-4-hydroxy-3,5-dinitro-2-[1,2:3,4-di-O-isopropyliden-β-L-arabinopyranosid-5-yl]-2H-1-benzopyran 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到3-nitro-2-[3-O-methyl-1,2-O-isopropyliden-β-L-threofuranosid-4-yl]-2H-chromene
  参考文献：
  名称：

  Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes

  摘要：

  A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of the sugar-derived (Z)-1-bromo-1-nitroalkenes with o-hydroxybenzaldehydes afforded enantiopure (2S,3S,4S)-3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans, which, upon SmI2-promoted beta-elimination, yielded chiral enantiopure 2-C-glycosyl-3-nitrochromenes.

  DOI：

  10.1021/jo4021634
• 作为产物：
  描述：

  2-Bromo-2-nitro-1-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]ethanol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 3-bromo-3,4-dihydro-4-hydroxy-3,5-dinitro-2-[1,2:3,4-di-O-isopropyliden-β-L-arabinopyranosid-5-yl]-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes

  摘要：

  A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of the sugar-derived (Z)-1-bromo-1-nitroalkenes with o-hydroxybenzaldehydes afforded enantiopure (2S,3S,4S)-3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans, which, upon SmI2-promoted beta-elimination, yielded chiral enantiopure 2-C-glycosyl-3-nitrochromenes.

  DOI：

  10.1021/jo4021634