methyl 4,7-anhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-D-arabino-L-altro-undec-2-ulo-2,5-furanoside | 1224923-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,7-anhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-D-arabino-L-altro-undec-2-ulo-2,5-furanoside
• CAS: 1224923-95-8
• 化学式: C₁₄H₂₅NO₉
• 分子量: 351.354
• InChiKey: ALQHCDNRQRLSEC-HHZVYRPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.74
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151.75
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 4,7-anhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-D-arabino-L-altro-undec-2-ulo-2,5-furanoside 、 乙酸酐 在 吡啶 作用下， 以38%的产率得到methyl (8,9,10,11-tetra-O-acetyl)-4,7-anhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-D-arabino-1-altro-undec-2-ulo-2,5-furanoside
  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：

  2,5-二甲基呋喃 、 甲醇 、 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-galacto-hept-1-enitol 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 20.0 ℃ 、1300.02 MPa 条件下， 反应 50.0h， 以8%的产率得到(2R,3S,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