(3AR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-5-(tosylmethyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran | 342808-81-5

• 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: (3AR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-5-(tosylmethyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran
• 英文别名: (1S,2R,6R,8S,9R)-4,4,11,11-tetramethyl-8-[(4-methylphenyl)sulfonylmethyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 342808-81-5
• 化学式: C₁₉H₂₆O₇S
• 分子量: 398.477
• InChiKey: VEUPRSPEUQBUQN-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3AR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-5-(tosylmethyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran 在 sodium azide 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5,5-diphenyl-3-[(2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b,4',5'-d]pyran-5-ylmethyl)carbamoyl]-4,5-dihydro-1H-pyrazole-4-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines

  摘要：

  Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64-20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76-84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,45,5S,6S,3aR,6a5)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.005
• 作为产物：
  描述：

  对甲苯磺酰氯 、 双丙酮半乳糖 以 吡啶 为溶剂， 反应 10.0h， 生成 (3AR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-5-(tosylmethyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran
  参考文献：
  名称：

  Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines

  摘要：

  Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64-20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76-84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,45,5S,6S,3aR,6a5)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.005