(1S,3R,4R,5R,6R,7S)-4,5-dihydroxy-3-hydroxymethyl-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid amide | 866916-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,5R,6R,7S)-4,5-dihydroxy-3-hydroxymethyl-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid amide
• 英文别名: (1S,3R,4S,5R,6R,7S)-4,5-dihydroxy-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptane-7-carboxamide
• CAS: 866916-60-1
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: SSTMBUVXWARJRO-GEGSFZHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R,6R,7S)-4,5-dihydroxy-3-hydroxymethyl-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid amide 在 sodium hydroxide 、 sodium hypochlorite 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到(1S,3R,4S,5R,6R,7S)-7-amino-3-hydroxymethyl-2-oxabicyclo[4.1.0]heptane-4,5-diol
  参考文献：
  名称：

  The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†

  摘要：

  Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining a-glucosidase from barley.

  DOI：

  10.1081/car-200067125
• 作为产物：
  描述：

  三-O-(叔丁基二甲基甲硅烷基)-D-葡萄烯糖 在 sodium cyanide 、 dirhodium tetraacetate 、 四丁基氟化铵 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 (1S,3R,4R,5R,6R,7S)-4,5-dihydroxy-3-hydroxymethyl-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid amide
  参考文献：
  名称：

  The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†

  摘要：

  Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining a-glucosidase from barley.

  DOI：

  10.1081/car-200067125

文献信息

• The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†
  作者：Robert Stick、Keith Stubbs

  DOI：10.1081/car-200067125

  日期：2005.8.1

  Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining a-glucosidase from barley.