(Z)-3-O-benzyl-6-bromo-5,6-dideoxy-1,2-O-isopropyliden-6-nitro-α-D-xylo-hex-5-enofuranose | 1509952-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-O-benzyl-6-bromo-5,6-dideoxy-1,2-O-isopropyliden-6-nitro-α-D-xylo-hex-5-enofuranose
• CAS: 1509952-23-1
• 化学式: C₁₆H₁₈BrNO₆
• 分子量: 400.226
• InChiKey: HFIYTGYRKXXDER-DPPMDJLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-O-benzyl-6-bromo-5,6-dideoxy-1,2-O-isopropyliden-6-nitro-α-D-xylo-hex-5-enofuranose 、 邻香草醛 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以74%的产率得到3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2-[3-O-methyl-1,2-O-isopropyliden-β-L-threofuranosid-4-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
• 作为产物：
  描述：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (Z)-3-O-benzyl-6-bromo-5,6-dideoxy-1,2-O-isopropyliden-6-nitro-α-D-xylo-hex-5-enofuranose
  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