[(3aR,4R,6R,7aS)-2,2,5-trimethylhexahydro[1,3]dioxolo[4,5-c]pyridine-4,6-diyl]dimethanol | 1416449-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,4R,6R,7aS)-2,2,5-trimethylhexahydro[1,3]dioxolo[4,5-c]pyridine-4,6-diyl]dimethanol
• CAS: 1416449-50-7
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: YSSZXMFSRRULTO-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.16
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,7aS)-2,2,5-trimethylhexahydro[1,3]dioxolo[4,5-c]pyridine-4,6-diyl]dimethanol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以71%的产率得到(2R,3R,4S,6R)-3,4-dihydroxy-2,6-bis(hydroxymethyl)-1-methylpiperidinium chloride
  参考文献：
  名称：

  Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (S)-Vinylglycinol

  摘要：

  An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the alpha-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.

  DOI：

  10.1021/ol303213r
• 作为产物：
  描述：

  methyl (3aS,5R,9aR,9bR)-2,2-dimethyl-7-oxohexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridine-5-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到[(3aR,4R,6R,7aS)-2,2,5-trimethylhexahydro[1,3]dioxolo[4,5-c]pyridine-4,6-diyl]dimethanol
  参考文献：
  名称：

  Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (S)-Vinylglycinol

  摘要：

  An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the alpha-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.

  DOI：

  10.1021/ol303213r