1-acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol | 150653-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol
• 英文别名: N-[[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]acetamide
• CAS: 150653-72-8
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: UQEQPFWCYJXMDK-LXGUWJNJSA-N

物化性质

• 沸点：
  509.8±45.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以90%的产率得到N-(((2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-methylpyrrolidin-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：

  (R)-N-(4-Phenyl-2-azido-3-butenyl)acetamide 在 palladium on activated charcoal 盐酸 、 二甲基硫 、 氢气 、 臭氧 、 三羟甲基氨基甲烷 、 sodium chloride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 25.0~37.0 ℃ 、392.24 kPa 条件下， 反应 38.0h， 生成 1-acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol
  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

• Schumacher-Wandersleb, Michael H.; Petersen, Stefan; Peter, Martin G., Liebigs Annalen der Chemie, 1994, # 6, p. 555 - 562
  作者：Schumacher-Wandersleb, Michael H.、Petersen, Stefan、Peter, Martin G.

  DOI：——

  日期：——
• 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.