(3R,4R,5S)-6-azido-1,3,4,5-tetrahydroxyhexan-2-one | 135395-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S)-6-azido-1,3,4,5-tetrahydroxyhexan-2-one
• CAS: 135395-64-1
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: DHCFCMVDOWDQHL-LFRDXLMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.06
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  146.75
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-6-azido-1,3,4,5-tetrahydroxyhexan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到米加司他
  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：

  [(3R,4R,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate 反应 24.0h， 以90%的产率得到(3R,4R,5S)-6-azido-1,3,4,5-tetrahydroxyhexan-2-one
  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

文献信息

• A chemoenzymic synthesis of 1,5-dideoxy-1,5-imino-l-mannitol and l-rhamnitol and investigation of their effects on glycosidases
  作者：Pengzu Zhou、Hamzah Mohd. Salleh、Phil C.M. Chan、Gilles Lajoie、John F. Honek、P.T.Chandra Nambiar、Owen P. Ward

  DOI：10.1016/0008-6215(93)84211-n

  日期：1993.2

  1,5-Dideoxy-1,5-imino-L-rhamnitol (3) and 1,5-dideoxy-1,5-imino-L-mannitol (2), designed as inhibitors of alpha-L-rhamnosidase, have been synthesised from dihydroxyacetone phosphate and 3-azido-2-hydroxypropanal with the aid of partially purified E. coli L-rhamnulose 1-phosphate aldolase free of D-fructose 1,6-bisphosphate aldolase activity. Inhibitory effects of compounds 2, 3, 1,5-dideoxy-1,5-imino-D-mannitol, and 1,5-dideoxy-1,5-imino-D-glucitol (12) were tested on selected glycosidases. It has been found that compound 3 is a good inhibitor of alpha-L-rhamnosidase as well as alpha-L-fucosidases from bovine kidney and epididymis, 2 is a potent inhibitor of alpha-galactosidase and a moderate inhibitor of alpha-L-rhamnosidase, and 12 is a good inhibitor of alpha-galactosidase and alpha-L-rhamnosidase.
• 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：——