(-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-methanol | 223138-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-methanol
• 英文别名: [(1S,2R,6S,8S)-10,10-dimethyl-3,7,9,11-tetraoxa-4-azatricyclo[6.3.0.02,6]undec-4-en-5-yl]methanol
• CAS: 223138-13-4
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: PUAVIHWBWBQURE-YWIQKCBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-methanol 以 水 、 三氟乙酸 为溶剂， 反应 15.0h， 生成 (-)-(3aS,5SR,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-dihydroxyfuro<2,3-d>isoxazole-3-methanol
  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 sodium tetrahydroborate 、 四氧化锇 、 4 A molecular sieve 、 Sikkon 、 硫酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 反应 16.5h， 生成 (-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-methanol
  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.