(+)-(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazole-3-carbaldehyde | 223421-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazole-3-carbaldehyde
• 英文别名: (1R,2S,6R,8R)-10,10-dimethyl-3,7,9,11-tetraoxa-4-azatricyclo[6.3.0.02,6]undec-4-ene-5-carbaldehyde
• CAS: 223421-32-7
• 化学式: C₉H₁₁NO₅
• 分子量: 213.19
• InChiKey: FWJHVLRRZPAEMD-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazole-3-carbaldehyde 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以66%的产率得到5-amino-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
  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：

  (+)-(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

文献信息

• Asymmetric Syntheses of New Polyhydroxylated Quinolizidines: Cross-Aldol Reactions of 7-Oxabicyclo[2.2.1]heptan-2-one and 3a,4a,7a,7b-Tetrahydro[1,3]dioxolo[4,5]furo[2,3-d]isoxazole-3-carbaldehyde Derivatives
  作者：Christophe Schaller、Pierre Vogel

  DOI：10.1002/(sici)1522-2675(20000119)83:1<193::aid-hlca193>3.0.co;2-i

  日期：2000.1.19

  Protocols were found for highly diastereoselective condensation giving the four possible aldols (+)-27 ('anti'), (+)-28 ('syn). 29 ('anti'). and (-)-30 ('syn') resulting from the exclusive exo-face reaction of the bicyclic lithium enolate of (-)-25 and bicyclic silyl ether (-)-31. Steric factors can explain the selectivities observed. Aldols (+)-27 (+)-28, 29, and (-)-30 were converted stereoselectively

  (-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1] heptan-2-one ((-) -25) 和 (+)-(3aR,4aR,7aR,7bS)- ((+)-26) 和 (-)-(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-四氢-6,6-dimethyl[1,3]dioxolo [4,5]furo[2,3-d]isoxazole-3-carbaldehyde ((-)-26) 用于 (-)-25 的烯醇锂和在 Mukaiyama 的条件下，它的三甲基甲硅烷基醚 (-)-31 (Scheme 2)。发现了高度非对映选择性缩合的协议，给出了四种可能的醛醇 (+)-27 ('anti')、(+)-28 ('syn)。29（“反”）。和 (-)-30 ('syn') 由 (-)-25 的双环烯醇锂和双环甲硅烷基醚
• Synthesis of a Polyhydroxyquinolizidine bearing a Polyhydroxylated Carbon Side-Chain
  作者：Christophe Schaller、Pierre Vogel

  DOI：10.1055/s-1999-3164

  日期：1999.8
• 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.