(+)-(2S,3S,4R)-3,4-epoxy-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione | 252268-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (+)-(2S,3S,4R)-3,4-epoxy-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione
• 英文别名: (2S,3S,5R)-2-(hydroxymethyl)-9-methyl-4-oxa-1,7,9-triazatricyclo[5.3.0.03,5]decane-8,10-dione
• CAS: 252268-49-8
• 化学式: C₈H₁₁N₃O₄
• 分子量: 213.193
• InChiKey: SNOZMLWRYJOAGK-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2S,3S,4R)-3,4-epoxy-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione 在 高氯酸 作用下， 以 水 为溶剂， 反应 5.0h， 生成 (+)-(2S,3S,4S)-3,4-dihydroxy-2-hydroxymethylmethyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Enantiopure 1-Azafagomine

  摘要：

  A new chemoenzymatic synthesis of both enantiomeric forms of the glycosidase inhibitor 1-azafagomine (1) is reported. The synthesis starts from the achiral starting materials pentadienol and methylurazol with the key steps being a hetero-Diels-Alder reaction followed by a lipase R/Novozym 435-catalyzed enantioselective esterification of the Diels-Alder adduct.

  DOI：

  10.1021/jo9907989
• 作为产物：
  描述：

  (R)-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione 在 Oxone 、 1,1,1-三氟丙酮 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以68%的产率得到(+)-(2S,3S,4R)-3,4-epoxy-2-hydroxymethyl-8-methyl-1,6,8-triazabicyclo[4.3.0]nonane-7,9-dione
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Enantiopure 1-Azafagomine

  摘要：

  A new chemoenzymatic synthesis of both enantiomeric forms of the glycosidase inhibitor 1-azafagomine (1) is reported. The synthesis starts from the achiral starting materials pentadienol and methylurazol with the key steps being a hetero-Diels-Alder reaction followed by a lipase R/Novozym 435-catalyzed enantioselective esterification of the Diels-Alder adduct.

  DOI：

  10.1021/jo9907989

文献信息

• Chemoenzymatic Synthesis of Enantiopure 1-Azafagomine
  作者：Xifu Liang、Mikael Bols

  DOI：10.1021/jo9907989

  日期：1999.11.1

  A new chemoenzymatic synthesis of both enantiomeric forms of the glycosidase inhibitor 1-azafagomine (1) is reported. The synthesis starts from the achiral starting materials pentadienol and methylurazol with the key steps being a hetero-Diels-Alder reaction followed by a lipase R/Novozym 435-catalyzed enantioselective esterification of the Diels-Alder adduct.