(Z)-7-bromo-6,7-dideoxy-1,2:3,4-di-O-isopropyliden-7-nitro-β-D-galacto-hept-6-enopyranose | 1509952-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (Z)-7-bromo-6,7-dideoxy-1,2:3,4-di-O-isopropyliden-7-nitro-β-D-galacto-hept-6-enopyranose
• 英文别名: (1S,2R,6R,8R,9S)-8-[(Z)-2-bromo-2-nitroethenyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 1509952-22-0
• 化学式: C₁₃H₁₈BrNO₇
• 分子量: 380.192
• InChiKey: OKSDKSRQXXORBP-LAFYKPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-7-bromo-6,7-dideoxy-1,2:3,4-di-O-isopropyliden-7-nitro-β-D-galacto-hept-6-enopyranose 在 samarium diiodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 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
• 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 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (Z)-7-bromo-6,7-dideoxy-1,2:3,4-di-O-isopropyliden-7-nitro-β-D-galacto-hept-6-enopyranose
  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.