1,2,3,5-tetradeoxy-1,5-imino-L-talo-octitol | 148216-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,2,3,5-tetradeoxy-1,5-imino-L-talo-octitol
• 英文别名: (1S,2S)-1-[(2S,3S)-3-hydroxypiperidin-2-yl]propane-1,2,3-triol
• CAS: 148216-39-1
• 化学式: C₈H₁₇NO₄
• 分子量: 191.227
• InChiKey: HMTATWCRRGEITD-DKXJUACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,5-tetradeoxy-1,5-imino-L-talo-octitol 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到(+)-2,8,8a-tri-epi-swainsonine
  参考文献：
  名称：

  Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine

  摘要：

  Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4+4 homologative procedure using 2-(trimethylsiloxy)furan (TMSOF), obtained from 2-furaldehyde, was employed to form the eight-carbon skeleton of the indolizidine triols and to install the proper chirality. Remarkably, the syntheses were completed by cyclizations of tetrahydroxypiperidine intermediates 8 and 14 to 9 and 15, respectively (ca. 90 %; PPh3, CCl4, Et3N in DMF at room temperature), without recourse to protecting groups.

  DOI：

  10.1021/jo00064a031
• 作为产物：
  描述：

  5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-L-talo-octono-1,4-lactone 在 dimethyl sulfide borane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 苯 为溶剂， 反应 2.75h， 生成 1,2,3,5-tetradeoxy-1,5-imino-L-talo-octitol
  参考文献：
  名称：

  Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine

  摘要：

  Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4+4 homologative procedure using 2-(trimethylsiloxy)furan (TMSOF), obtained from 2-furaldehyde, was employed to form the eight-carbon skeleton of the indolizidine triols and to install the proper chirality. Remarkably, the syntheses were completed by cyclizations of tetrahydroxypiperidine intermediates 8 and 14 to 9 and 15, respectively (ca. 90 %; PPh3, CCl4, Et3N in DMF at room temperature), without recourse to protecting groups.

  DOI：

  10.1021/jo00064a031

文献信息

• Total syntheses of (+)-2,8,8a-tri-epi-swainsonine and (-)-1-epi-swainsonine
  作者：Giovanni Casiraghi、Gloria Rassu、Pietro Spanu、Luigi Pinna、Fausta Ulgheri

  DOI：10.1021/jo00064a031

  日期：1993.6

  Parallel syntheses of the title swainsonine-related enantiomers 9 and 15 were achieved in five steps and in 55% overall yield via enantiomeric threose N-benzylimines 4 and 10, derived from L- and D-tartaric acid, respectively. A stereospecific 4+4 homologative procedure using 2-(trimethylsiloxy)furan (TMSOF), obtained from 2-furaldehyde, was employed to form the eight-carbon skeleton of the indolizidine triols and to install the proper chirality. Remarkably, the syntheses were completed by cyclizations of tetrahydroxypiperidine intermediates 8 and 14 to 9 and 15, respectively (ca. 90 %; PPh3, CCl4, Et3N in DMF at room temperature), without recourse to protecting groups.