(1S,2S,4R,5R)-4-(hydroxy)-6,7-diazabicyclo[3.2.1]oct-6-en-2-yl acetate | 894423-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R,5R)-4-(hydroxy)-6,7-diazabicyclo[3.2.1]oct-6-en-2-yl acetate
• 英文别名: [(1S,2S,4R,5R)-4-hydroxy-6,7-diazabicyclo[3.2.1]oct-6-en-2-yl] acetate
• CAS: 894423-95-1
• 化学式: C₈H₁₂N₂O₃
• 分子量: 184.195
• InChiKey: ZVNVELXOPDLIOX-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5R)-4-(hydroxy)-6,7-diazabicyclo[3.2.1]oct-6-en-2-yl acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 21.0 ℃ 、379.21 kPa 条件下， 反应 5.0h， 生成 [(1S,2S,4R,5R)-2,4-diamino-5-hydroxycyclohexyl] acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of 2,5-dideoxystreptamine precursors

  摘要：

  The stereoselective enzymatic acylation of meso-6,7-diazabicyclo[3.2.1]oct-6-ene-2,4-diol 4 and meso-4,6-diazidocyclohexane-1,3-diol 5 in organic media gave the corresponding monoesters in high enantiomeric excess. The hydrolysis of the corresponding diacetate derivatives in the presence of a different set of enzymes provided the same monoesters. The products are precursors of dideoxystreptamine, an aminocyclitol found in synthetic aminoglycoside antibiotics. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.014
• 作为产物：
  描述：

  cis-1,4-cyclohexadiene diepoxide 在 双氧水 、 肼 、 磷脂酶B 作用下， 以 乙醇 、 水 为溶剂， 反应 164.0h， 生成 (1S,2S,4R,5R)-4-(hydroxy)-6,7-diazabicyclo[3.2.1]oct-6-en-2-yl acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of 2,5-dideoxystreptamine precursors

  摘要：

  The stereoselective enzymatic acylation of meso-6,7-diazabicyclo[3.2.1]oct-6-ene-2,4-diol 4 and meso-4,6-diazidocyclohexane-1,3-diol 5 in organic media gave the corresponding monoesters in high enantiomeric excess. The hydrolysis of the corresponding diacetate derivatives in the presence of a different set of enzymes provided the same monoesters. The products are precursors of dideoxystreptamine, an aminocyclitol found in synthetic aminoglycoside antibiotics. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.014

文献信息

• Falk-Heppner, Manuela; Keller, Manfred; Prinzbach, Horst, Angewandte Chemie, 1989, vol. 101, # 9, p. 1281 - 1283
  作者：Falk-Heppner, Manuela、Keller, Manfred、Prinzbach, Horst

  DOI：——

  日期：——