[(3R,4S,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate | 136616-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3R,4S,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate
• CAS: 136616-68-7
• 化学式: C₆H₁₂N₃O₈P
• 分子量: 285.15
• InChiKey: MMLKQLPVGJWKTH-FUTKDDECSA-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：

  [(3R,4S,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate 在 palladium on activated charcoal 氢气 作用下， 以90%的产率得到1,5,6-trideoxy-1,5-imino-L-mannitol
  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：

  (2R)-3-叠氮基-2-羟基丙醛 在 sodium hydroxide 、 O-fructose-1,6-diphosphate-Na₃ 作用下， 反应 24.0h， 生成 [(3R,4S,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate
  参考文献：
  名称：

  改进的新果糖衍生物的化学和酶促合成方法，用于葡萄糖转运蛋白在寄生虫中的进口研究

  摘要：

  本文介绍了在位置C6处取代的D-果糖类似物的化学酶法合成。这些化合物是兔肌肉醛缩酶用DHAP催化D-甘油醛类似物（通过立体定向化学合成获得）醛缩醛化，然后用酸性磷酸酶进行去磷酸化步骤的独特产物。

  DOI：

  10.1016/0040-4020(95)01001-7

文献信息

• KAJIMOTO, TETSUYA;CHEN, LIHREN;LIU, KEVIN K. -C.;WONG, CHI-HUEY, J. AMER. CHEM. SOC., 113,(1991) N7, C. 6678-6680
  作者：KAJIMOTO, TETSUYA、CHEN, LIHREN、LIU, KEVIN K. -C.、WONG, CHI-HUEY

  DOI：——

  日期：——