1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-α-D-allo-1,4-furanose | 1346677-50-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-α-D-allo-1,4-furanose
• CAS: 1346677-50-6
• 化学式: C₁₁H₂₀O₇
• 分子量: 264.276
• InChiKey: FDDCMBICLPKHIK-ZBGLXGBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-α-D-allo-1,4-furanose 在 sodium periodate 、 水 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 7.5h， 生成 1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-5-N-benzyl-N-benzyloxycarbonyl-α-D-ribo-1,4-furanose
  参考文献：
  名称：

  Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors

  摘要：

  Anomeric 1,5-anhydrosugar 2 was synthesized from D-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy-and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of alpha-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.046
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium periodate 、 高氯酸 、 水 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.5h， 生成 1,2-O-isopropylidene-3-C-(1'-hydroxyethyl)-α-D-allo-1,4-furanose
  参考文献：
  名称：

  Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors

  摘要：

  Anomeric 1,5-anhydrosugar 2 was synthesized from D-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy-and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of alpha-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.046