(+)-(3aR,4'S,5R,5'S,6R,6aS)-3-(4',5'-diphenylimidazolid-2'-yl)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole | 223142-14-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+)-(3aR,4'S,5R,5'S,6R,6aS)-3-(4',5'-diphenylimidazolid-2'-yl)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole
• 英文别名: (1R,2S,6R,8R)-5-[(4S,5S)-4,5-diphenylimidazolidin-2-yl]-10,10-dimethyl-3,7,9,11-tetraoxa-4-azatricyclo[6.3.0.02,6]undec-4-ene
• CAS: 223142-14-1
• 化学式: C₂₃H₂₅N₃O₄
• 分子量: 407.469
• InChiKey: KNRVACSFPRQBBV-TYMIJZIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-(3aR,4'S,5R,5'S,6R,6aS)-3-(4',5'-diphenylimidazolid-2'-yl)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole 在 硫酸 作用下， 以 乙醚 、 水 为溶剂， 反应 0.5h， 生成 (+)-(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazole-3-carbaldehyde
  参考文献：
  名称：

  Total syntheses of (+)- and (−)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-d- and l-glucitol) and of (+)- and (−)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-d- and l-iditol) via furoisoxazoline-3-aldehydes

  摘要：

  The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00287-0
• 作为产物：
  描述：

  (+/-)-3-(diethoxymethyl)-3a,6a-dihydrofuro<2,3-d>isoxazole 在 四氧化锇 、 4 A molecular sieve 、 Sikkon 、 硫酸 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 16.0h， 生成 (+)-(3aR,4'S,5R,5'S,6R,6aS)-3-(4',5'-diphenylimidazolid-2'-yl)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole
  参考文献：
  名称：

  Total syntheses of (+)- and (−)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-d- and l-glucitol) and of (+)- and (−)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-d- and l-iditol) via furoisoxazoline-3-aldehydes

  摘要：

  The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00287-0

文献信息

• Total syntheses of (+)- and (−)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-d- and l-glucitol) and of (+)- and (−)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-d- and l-iditol) via furoisoxazoline-3-aldehydes
  作者：Christophe Schaller、Pierre Vogel、Volker Jäger

  DOI：10.1016/s0008-6215(98)00287-0

  日期：1998.12

  The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. All rights reserved.