2,6-bis{(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-1,6-dioxa-2-azaspiro[4,5]dec-2-en-3-yl}pyridine | 1207109-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis{(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-1,6-dioxa-2-azaspiro[4,5]dec-2-en-3-yl}pyridine
• 英文别名: [(5R,6R,7S,8R,9R)-6,7,8-triacetyloxy-3-[6-[(5R,6R,7S,8R,9R)-6,7,8-triacetyloxy-9-(acetyloxymethyl)-1,10-dioxa-2-azaspiro[4.5]dec-2-en-3-yl]pyridin-2-yl]-1,10-dioxa-2-azaspiro[4.5]dec-2-en-9-yl]methyl acetate
• CAS: 1207109-60-1
• 化学式: C₃₇H₄₃N₃O₂₀
• 分子量: 849.757
• InChiKey: IRJGGBKKUBLGMT-MVVPIXPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  285
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2,6-bis{(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-1,6-dioxa-2-azaspiro[4,5]dec-2-en-3-yl}pyridine 在 palladium diacetate 作用下， 以 氘代氯仿 为溶剂， 生成 2,6-bis{3-[(1'R)-1',2',3',5'-tetra-O-acetyl-D-arabino-1'-C-isoxazol-5-yl]}pyridine
  参考文献：
  名称：

  Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis

  摘要：

  Two carbohydrate-based spiro bis(isoxazolines) were synthesized via 1,3-dipolar cycloaddition from peracetylated methylene exo-glucal and the corresponding bis(arylnitrile oxide). The bis(cycloadducts) were then evaluated as ligands for enantioselective catalytic reactions. The Pd-catalyzed Tsuji-Trost reaction between a malonate and an allylic acetate did not provide good results. The poor conversion observed can be attributed to the rearrangement of the ligand in the reaction mixture to afford the corresponding ring-opened isoxazole which has been characterized. Both ligands were also evaluated in Cu(I)-catalyzed asymmetric imine alkynylation and afforded the product in good yield and modest enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.028
• 作为产物：
  描述：

  N,N-dihydroxypyridine-1,3-dicarboximidoyl dichloride 、 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-D- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以71%的产率得到2,6-bis{(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-1,6-dioxa-2-azaspiro[4,5]dec-2-en-3-yl}pyridine
  参考文献：
  名称：

  Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis

  摘要：

  Two carbohydrate-based spiro bis(isoxazolines) were synthesized via 1,3-dipolar cycloaddition from peracetylated methylene exo-glucal and the corresponding bis(arylnitrile oxide). The bis(cycloadducts) were then evaluated as ligands for enantioselective catalytic reactions. The Pd-catalyzed Tsuji-Trost reaction between a malonate and an allylic acetate did not provide good results. The poor conversion observed can be attributed to the rearrangement of the ligand in the reaction mixture to afford the corresponding ring-opened isoxazole which has been characterized. Both ligands were also evaluated in Cu(I)-catalyzed asymmetric imine alkynylation and afforded the product in good yield and modest enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.028
• 作为试剂：
  描述：

  N-苄叉苯胺 、 苯乙炔 在 copper(I) trifluoromethanesulfonate benzene 、 2,6-bis{(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-1,6-dioxa-2-azaspiro[4,5]dec-2-en-3-yl}pyridine 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以52%的产率得到N-(1,3-diphenylprop-2-yn-1-yl)benzenamine
  参考文献：
  名称：

  Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis

  摘要：

  Two carbohydrate-based spiro bis(isoxazolines) were synthesized via 1,3-dipolar cycloaddition from peracetylated methylene exo-glucal and the corresponding bis(arylnitrile oxide). The bis(cycloadducts) were then evaluated as ligands for enantioselective catalytic reactions. The Pd-catalyzed Tsuji-Trost reaction between a malonate and an allylic acetate did not provide good results. The poor conversion observed can be attributed to the rearrangement of the ligand in the reaction mixture to afford the corresponding ring-opened isoxazole which has been characterized. Both ligands were also evaluated in Cu(I)-catalyzed asymmetric imine alkynylation and afforded the product in good yield and modest enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.028

文献信息

• Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis
  作者：David Goyard、Susanne M. Telligmann、Catherine Goux-Henry、Mike M.K. Boysen、Eric Framery、David Gueyrard、Sébastien Vidal

  DOI：10.1016/j.tetlet.2009.11.028

  日期：2010.1

  Two carbohydrate-based spiro bis(isoxazolines) were synthesized via 1,3-dipolar cycloaddition from peracetylated methylene exo-glucal and the corresponding bis(arylnitrile oxide). The bis(cycloadducts) were then evaluated as ligands for enantioselective catalytic reactions. The Pd-catalyzed Tsuji-Trost reaction between a malonate and an allylic acetate did not provide good results. The poor conversion observed can be attributed to the rearrangement of the ligand in the reaction mixture to afford the corresponding ring-opened isoxazole which has been characterized. Both ligands were also evaluated in Cu(I)-catalyzed asymmetric imine alkynylation and afforded the product in good yield and modest enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.