5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-L-talo-octono-1,4-lactone | 148216-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-L-talo-octono-1,4-lactone
• 英文别名: (5S)-5-[(S)-amino-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]oxolan-2-one
• CAS: 148216-38-0
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: HFHDIDLSAQWSBD-ZRUAGYDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-L-talo-octono-1,4-lactone 在 四氯化碳 、 dimethyl sulfide borane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.75h， 生成 (+)-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：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 sodium acetate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-L-talo-octono-1,4-lactone
  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.