(3aS,5R,6S,7S,7aR)-5-(hydroxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[2,3-d]oxazole-6,7-diol | 849367-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,5R,6S,7S,7aR)-5-(hydroxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[2,3-d]oxazole-6,7-diol
• 英文别名: (3aS,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol
• CAS: 849367-23-3
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: IBKJGGFQDRZURS-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.76
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91.51
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,5R,6S,7S,7aR)-5-(hydroxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[2,3-d]oxazole-6,7-diol 生成 N-acetyl-α-D-glucopyranosylamide
  参考文献：
  名称：

  α-Glucopyranoimidazolines as intermediate analogue inhibitors of family 20 β-N-acetylglucosaminidases

  摘要：

  The alpha-glucopyranoimidazolines, 2-methyl-(1,2-dideoxy-alpha-D-glucopyrano)[2,1-d]-1-imidazolines 1 and 2, have been synthesized and evaluated as inhibitors of beta-N-acetylglucosaminidases (NAGs). Compounds I and 2, mimicking the oxazolinium ion intermediate in enzyme catalysis, served as potent and competitive inhibitors of family 20 NAGs with K-i as low as 0.1 muM, but showed no inhibitory activities toward family 3 NAGs. Due to structural and electrostatic resemblance to the oxazolinium ion intermediate, the alpha-glucopyranoimidazolines may lead to novel and selective inhibitors of mechanistically related glycosidases such as family 18 chitinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.017
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-α-D-glucopyranosyl isoxazoline 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以63%的产率得到(3aS,5R,6S,7S,7aR)-5-(hydroxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[2,3-d]oxazole-6,7-diol
  参考文献：
  名称：

  α-Glucopyranoimidazolines as intermediate analogue inhibitors of family 20 β-N-acetylglucosaminidases

  摘要：

  The alpha-glucopyranoimidazolines, 2-methyl-(1,2-dideoxy-alpha-D-glucopyrano)[2,1-d]-1-imidazolines 1 and 2, have been synthesized and evaluated as inhibitors of beta-N-acetylglucosaminidases (NAGs). Compounds I and 2, mimicking the oxazolinium ion intermediate in enzyme catalysis, served as potent and competitive inhibitors of family 20 NAGs with K-i as low as 0.1 muM, but showed no inhibitory activities toward family 3 NAGs. Due to structural and electrostatic resemblance to the oxazolinium ion intermediate, the alpha-glucopyranoimidazolines may lead to novel and selective inhibitors of mechanistically related glycosidases such as family 18 chitinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.017