(1R,3R,4S,5S,8R)-3-Octylamino-6-oxa-bicyclo[3.2.1]octane-4,8-diol | 794535-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,4S,5S,8R)-3-Octylamino-6-oxa-bicyclo[3.2.1]octane-4,8-diol
• CAS: 794535-93-6
• 化学式: C₁₅H₂₉NO₃
• 分子量: 271.4
• InChiKey: SEYOOKGOPRUZLN-ZSAUSMIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.72
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S,5S,8R)-3-Octylamino-6-oxa-bicyclo[3.2.1]octane-4,8-diol 在 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 N-octyl-6-deoxy-5a-carba-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.02,4]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

  摘要：

  Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2muM, green coffee beans). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.091
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-bromo-6-deoxy-5a-carba-β-DL-glucopyranosyl bromide 在 sodium methylate 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 3.0h， 生成 (1R,3R,4S,5S,8R)-3-Octylamino-6-oxa-bicyclo[3.2.1]octane-4,8-diol
  参考文献：
  名称：

  Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.02,4]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

  摘要：

  Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2muM, green coffee beans). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.091