8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one | 162992-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one
• 英文别名: (5R,6R,7R,7aS)-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 162992-52-1
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: XAMFRTUWKMLMFC-HVWQDESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 反应 24.0h， 以90%的产率得到5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007
• 作为产物：
  描述：

  2,5-二(羟基甲基)-3,4-吡咯烷二醇 在 sodium hydride 、 碳酸氢钠 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007

文献信息

• Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors
  作者：Chi-Huey Wong、Louis Provencher、John A. Porco、Sang-Hun Jung、Yi-Fong Wang、Lihren Chen、Ruo Wang、Darryl H. Steensma

  DOI：10.1021/jo00111a007

  日期：1995.3

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.