N-((2R,3R,4S)-2-Azido-3,4,6-trihydroxy-5-oxo-hexyl)-acetamide | 150571-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2R,3R,4S)-2-Azido-3,4,6-trihydroxy-5-oxo-hexyl)-acetamide
• 英文别名: N-[(2R,3R,4S)-2-azido-3,4,6-trihydroxy-5-oxohexyl]acetamide
• CAS: 150571-21-4
• 化学式: C₈H₁₄N₄O₅
• 分子量: 246.223
• InChiKey: OBVBBCGGRFMRGP-LPBLVHEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((2R,3R,4S)-2-Azido-3,4,6-trihydroxy-5-oxo-hexyl)-acetamide 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到N-(((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)acetamide
  参考文献：
  名称：

  Iminocyclitol inhibitors of hexoaminidase and glycosidase

  摘要：

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。

  公开号：

  US06774140B1
• 作为产物：
  描述：

  N-(2-azido-3-oxo-propyl)-acetamide 在 盐酸 、 三羟甲基氨基甲烷 、 sodium chloride 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N-((2R,3R,4S)-2-Azido-3,4,6-trihydroxy-5-oxo-hexyl)-acetamide
  参考文献：
  名称：

  Inhibition of N-acetylglucosaminyl transfer enzymes: chemical-enzymic synthesis of new five-membered acetamido azasugars

  摘要：

  Two new acetamido azasugars have been synthesized and tested as inhibitors of beta-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a beta-N-acetylglucosaminidase with K(i) values of 1.9 and 3.6 muM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.

  DOI：

  10.1021/jo00070a013

文献信息

• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• Inhibition of N-acetylglucosaminyl transfer enzymes: chemical-enzymic synthesis of new five-membered acetamido azasugars
  作者：Yoshikazu Takaoka、Tetsuya Kajimoto、Chi Huey Wong

  DOI：10.1021/jo00070a013

  日期：1993.8

  Two new acetamido azasugars have been synthesized and tested as inhibitors of beta-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a beta-N-acetylglucosaminidase with K(i) values of 1.9 and 3.6 muM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.