3-nitro-2-[3-O-methyl-1,2-O-isopropyliden-β-L-threofuranosid-4-yl]-2H-chromene | 1509952-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-nitro-2-[3-O-methyl-1,2-O-isopropyliden-β-L-threofuranosid-4-yl]-2H-chromene
• 英文别名: (1S,2R,6R,8R,9S)-8-[(2R)-3,6-dinitro-2H-chromen-2-yl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 1509952-37-7
• 化学式: C₂₀H₂₂N₂O₁₀
• 分子量: 450.402
• InChiKey: XMRCUXFHAQXFIE-GVLSGGHMSA-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：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,2：3,4-二-O-异亚丙基-α-D-半乳糖-己二醛-1,5-吡喃糖 在 samarium diiodide 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 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

文献信息

• Synthesis of Enantiopure 2-<i>C</i>-Glycosyl-3-nitrochromenes
  作者：Raquel G. Soengas、Humberto Rodríguez-Solla、Artur M. S. Silva、Ricardo Llavona、Filipe A. Almeida Paz

  DOI：10.1021/jo4021634

  日期：2013.12.20

  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.