Phosphoric acid mono-((3R,4S,5R)-6-azido-3,4,5-trihydroxy-2-oxo-hexyl) ester | 136616-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid mono-((3R,4S,5R)-6-azido-3,4,5-trihydroxy-2-oxo-hexyl) ester
• CAS: 136616-70-1
• 化学式: C₆H₁₂N₃O₈P
• 分子量: 285.15
• InChiKey: MMLKQLPVGJWKTH-PYWDMBMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  193.28
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-((3R,4S,5R)-6-azido-3,4,5-trihydroxy-2-oxo-hexyl) ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 37.0 ℃ 、344.73 kPa 条件下， 反应 24.0h， 生成 1-deoxynojirimycin
  参考文献：
  名称：

  Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars

  摘要：

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.

  DOI：

  10.1021/jo00022a013
• 作为产物：
  描述：

  1-羟基-3-(磷酰氧基)-2-丙酮 、 (2R)-3-叠氮基-2-羟基丙醛 以 水 为溶剂， 反应 1.0h， 生成 Phosphoric acid mono-((3R,4S,5R)-6-azido-3,4,5-trihydroxy-2-oxo-hexyl) ester
  参考文献：
  名称：

  Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars

  摘要：

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.

  DOI：

  10.1021/jo00022a013