2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol | 140193-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol
• 英文别名: Syfutigrlbpvfx-lxunurovsa-；(3aS,6S,7R,7aR)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 140193-74-4
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: SYFUTIGRLBPVFX-LXUNUROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 以71%的产率得到N-5-O-diacetyl-2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol
  参考文献：
  名称：

  Total synthesis of 1,5-dideoxy-1,5-iminoalditols

  摘要：

  Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.

  DOI：

  10.1016/s0040-4020(01)88132-1
• 作为产物：
  描述：

  (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 在 二环己烷并-18-冠醚-6 、 palladium dihydroxide potassium permanganate 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol
  参考文献：
  名称：

  Total synthesis of 1,5-dideoxy-1,5-iminoalditols

  摘要：

  Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.

  DOI：

  10.1016/s0040-4020(01)88132-1

文献信息

• Total synthesis of 1,5-dideoxy-1,5-iminoalditols
  作者：Gloria Rassu、Luigi Pinna、Pietro Spanu、Nicola Culeddu、Giovanni Casiraghi、Giovanna Gasparri Fava、Marisa Belicchi Ferrari、Giorgio Pelosi

  DOI：10.1016/s0040-4020(01)88132-1

  日期：——

  Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.