8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one | 162895-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one
• 英文别名: (5R,6R,7R,7aS)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 162895-65-0
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: ITNKSPYGXYWVIF-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one 在 氢氧化钾 、 sodium hydride 、 potassium iodide 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 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：

  (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 在 钯 dilithium tetrabromonickelate(II) 、 氢气 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 12.5h， 生成 8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one
  参考文献：
  名称：

  Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives

  摘要：

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00267-9

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.
• Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives
  作者：Isabelle McCort、Sébastien Fort、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00267-9

  日期：2000.1

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.