methyl (1'R,2'R,3'S,4'R)-3-phenyl-5-[(1',2'-4',5'-diisopropylidenedioxy,3'-hydroxy)pentyl]-isoxazole-4-carboxylate | 865189-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1'R,2'R,3'S,4'R)-3-phenyl-5-[(1',2'-4',5'-diisopropylidenedioxy,3'-hydroxy)pentyl]-isoxazole-4-carboxylate
• 英文别名: methyl 5-[(4R,5R)-5-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenyl-1,2-oxazole-4-carboxylate
• CAS: 865189-23-7
• 化学式: C₂₂H₂₇NO₈
• 分子量: 433.458
• InChiKey: CFVKPAAYFGIBBQ-HQJJXPTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1'R,2'R,3'S,4'R)-3-phenyl-5-[(1',2'-4',5'-diisopropylidenedioxy,3'-hydroxy)pentyl]-isoxazole-4-carboxylate 在 三氟乙酸 作用下， 以100%的产率得到methyl (1'R,2'R,3'S,4'R)-3-phenyl-5-[(1',2',3',4',5'-pentahydroxy)pentyl]-isoxazole-4-carboxylate
  参考文献：
  名称：

  Cycloaddition reactions on activated exo-glycals

  摘要：

  Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.027
• 作为产物：
  描述：

  benzohydroximoyl chloride 、 methyl (2Z)-2-[(3aR,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到methyl (1'R,2'R,3'S,4'R)-3-phenyl-5-[(1',2'-4',5'-diisopropylidenedioxy,3'-hydroxy)pentyl]-isoxazole-4-carboxylate
  参考文献：
  名称：

  Cycloaddition reactions on activated exo-glycals

  摘要：

  Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.027

文献信息

• Cycloaddition reactions on activated exo-glycals
  作者：Gérald Enderlin、Claude Taillefumier、Claude Didierjean、Yves Chapleur

  DOI：10.1016/j.tetasy.2005.06.027

  日期：2005.7

  Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.