(9,10,11-tri-O-acetyl)-4,7:2,8-dianhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-α-D-lyxo-D-galacto-undec-2-ulo-2,5-furanoside | 1032072-98-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (9,10,11-tri-O-acetyl)-4,7:2,8-dianhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-α-D-lyxo-D-galacto-undec-2-ulo-2,5-furanoside
• CAS: 1032072-98-2
• 化学式: C₁₉H₂₇NO₁₁
• 分子量: 445.423
• InChiKey: LQTZRLMIKGVKHH-CUZKMJQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  149.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  (2S,3R)-2-(endo-D-galacto-pentaacetoxypentyl)-1,4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene 、 乙酸酐 在 甲醇 、 potassium carbonate 、 吡啶 作用下， 反应 2.0h， 以60%的产率得到(9,10,11-tri-O-acetyl)-7-acetoxy-4,8-anhydro-1,3,6-trideoxy-5-C-methyl-6-C-nitromethyl-D-lyxo-D-galacto-undec-2-ulo-2,5-furanose
  参考文献：
  名称：

  Unexpected Reactions: From (2S,3R)-2-(endo-d-Galacto-pentaacetoxypentyl)-1,4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene to Chiral Cyclic Ethers

  摘要：

  在高压Diels-Alder反应中，2,5-二甲基呋喃与d-galacto-3,4,5,6,7-五-O-乙酰基-1,2-去氧-1-硝基庚-1-烯醇反应，经过从粗产物中进行分馏结晶，得到纯净的(2S,3R)-2-(endo-d-galacto-五乙酰氧基戊基)-1,4-二甲基-3-exo-硝基-7-氧双环[2.2.1]庚-5-烯。其结构通过化学途径和X射线粉末衍射法确定。该加合物糖侧链的去乙酰化导致了双环体系的开环，随后发生了分子内亲核加成的串联反应，从而生成新的手性双环和三环醚。

  DOI：

  10.1055/s-2008-1042798

文献信息

• Synthesis and ring opening reactions of 2-glyco-1,4-dimethyl-3-nitro-7-oxabicyclo[2.2.1]hept-5-enes
  作者：Noelia Araújo、María V. Gil、Emilio Román、José A. Serrano

  DOI：10.1016/j.tet.2010.02.027

  日期：2010.4

  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