(2R,3R,4S,5R)-4,5-epoxy-4,7-dimethyl-3-nitromethyl-2-(D-arabino-tetritol-1'-yl)-2,3-dihydrooxepine | 1224924-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-4,5-epoxy-4,7-dimethyl-3-nitromethyl-2-(D-arabino-tetritol-1'-yl)-2,3-dihydrooxepine
• CAS: 1224924-07-5
• 化学式: C₁₃H₂₁NO₈
• 分子量: 319.312
• InChiKey: KSKDDEXMGNHGBR-LAFJZYIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  145.82
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-4,5-epoxy-4,7-dimethyl-3-nitromethyl-2-(D-arabino-tetritol-1'-yl)-2,3-dihydrooxepine 、 乙酸酐 在 吡啶 作用下， 以13%的产率得到(2R,3R,4S,5R)-(1',2',3',4'-tetra-O-acetyl-D-arabinotetritol-1'-yl)-4,5-epoxy-4,7-dimethyl-3-nitromethyl-2,3-dihydrooxepine
  参考文献：
  名称：

  Synthesis and ring opening reactions of 2-glyco-1,4-dimethyl-3-nitro-7-oxabicyclo[2.2.1]hept-5-enes

  摘要：

  The high-pressure asymmetric Diels-Alder reactions of D-galacto-(1a) and D-manno-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitrohept-1-enitol (1b) with 2,5-dimethylfuran (2) afforded mixtures of cycloadducts, from which the (25,3R)-3-exo-nitro (3a and 3b), (2R,3S)-3-exo-nitro (4a and 4b), and (2R,3S)-1',2',3',4',5'-penta-O-acetyl-1'-C-(1.4-dimethyl-3-endo-nitro-7-oxabicyclo[2 2 1]hept-5-en-2-exo-yl)-D-galacto-pentitol (5b) were isolated pure Deacetylanon of these compounds led to new chual mono-, b1-, and tricyclic ethers, being their asymmetric centers arising from the chiral inductor used in the cycloaddition reaction A ring opening mechanism through a 1-nitro-1,3-cyclohexadiene intermediate has been proposed (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.027
• 作为产物：
  描述：

  (2R,3S)-1',2',3',4',5'-penta-O-acetyl-1'-C-(1,4-dimethyl-3-endo-nitro-7-oxabicyclo[2.2.1]hept-5-en-2-exo-yl)-D-mannopentitol 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以87%的产率得到(2R,3R,4S,5R)-4,5-epoxy-4,7-dimethyl-3-nitromethyl-2-(D-arabino-tetritol-1'-yl)-2,3-dihydrooxepine
  参考文献：
  名称：

  Synthesis and ring opening reactions of 2-glyco-1,4-dimethyl-3-nitro-7-oxabicyclo[2.2.1]hept-5-enes

  摘要：

  The high-pressure asymmetric Diels-Alder reactions of D-galacto-(1a) and D-manno-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitrohept-1-enitol (1b) with 2,5-dimethylfuran (2) afforded mixtures of cycloadducts, from which the (25,3R)-3-exo-nitro (3a and 3b), (2R,3S)-3-exo-nitro (4a and 4b), and (2R,3S)-1',2',3',4',5'-penta-O-acetyl-1'-C-(1.4-dimethyl-3-endo-nitro-7-oxabicyclo[2 2 1]hept-5-en-2-exo-yl)-D-galacto-pentitol (5b) were isolated pure Deacetylanon of these compounds led to new chual mono-, b1-, and tricyclic ethers, being their asymmetric centers arising from the chiral inductor used in the cycloaddition reaction A ring opening mechanism through a 1-nitro-1,3-cyclohexadiene intermediate has been proposed (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.027