(3S,3aR,6aS,6R)-ethyl 2-benzyl-6-pivaloyloxymethyl-4-oxotetrahydrofuro[3,4-d]isoxazolidine-3-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3aR,6aS,6R)-ethyl 2-benzyl-6-pivaloyloxymethyl-4-oxotetrahydrofuro[3,4-d]isoxazolidine-3-carboxylate
• 英文别名: ethyl (3S,3aR,6R,6aS)-2-benzyl-6-(2,2-dimethylpropanoyloxymethyl)-4-oxo-3,3a,6,6a-tetrahydrofuro[3,4-d][1,2]oxazole-3-carboxylate
• 化学式: C₂₁H₂₇NO₇
• 分子量: 405.448
• InChiKey: WHKUWVDPWLDDJE-WCXIOVBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 在 吡啶 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 44.0h， 生成 (3S,3aR,6aS,6R)-ethyl 2-benzyl-6-pivaloyloxymethyl-4-oxotetrahydrofuro[3,4-d]isoxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselectivity of N-benzyl-C-ethoxycarbonyl nitrone cycloaddition to (S)-5-hydroxymethyl-2(5H)-furanone and its derivatives

  摘要：

  Stereoselectivity of the reaction of N-benzyl-C-ethoxycarbonyl nitrone (3) with (S)-5-hydroxymethyl-2(5H)-furanone (2a) and its 5-alkoxy substituted derivatives 2b-f was investigated. The reaction proceeds in a highly face-selective manner, the products 4-6 resulting from approach anti to the hydroxymethyl or alkoxymethyl group of the dipolarophile. The exo-stereoselectivity increases as the size of protective group attached to lactone (2b-f) increases. Endo-exo diastereoselectivity is affected significantly by the solvent. Microwave irradiation strongly accelerates the reaction with little effect on the diastereoselectivity to give the syn adduct 8a in addition to anti cycloadducts 4a-6a. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00568-2

文献信息

• Stereoselectivity of N-benzyl-C-ethoxycarbonyl nitrone cycloaddition to (S)-5-hydroxymethyl-2(5H)-furanone and its derivatives
  作者：Vladimír Ondruš、Michal Orság、L'ubor Fišera、Nad'a Prónayová

  DOI：10.1016/s0040-4020(99)00568-2

  日期：1999.8

  Stereoselectivity of the reaction of N-benzyl-C-ethoxycarbonyl nitrone (3) with (S)-5-hydroxymethyl-2(5H)-furanone (2a) and its 5-alkoxy substituted derivatives 2b-f was investigated. The reaction proceeds in a highly face-selective manner, the products 4-6 resulting from approach anti to the hydroxymethyl or alkoxymethyl group of the dipolarophile. The exo-stereoselectivity increases as the size of protective group attached to lactone (2b-f) increases. Endo-exo diastereoselectivity is affected significantly by the solvent. Microwave irradiation strongly accelerates the reaction with little effect on the diastereoselectivity to give the syn adduct 8a in addition to anti cycloadducts 4a-6a. (C) 1999 Elsevier Science Ltd. All rights reserved.