5-chloro-5-deoxy-1,2:3,4-di-O-isopropylidene-L-muco-quercitol | 861661-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-5-deoxy-1,2:3,4-di-O-isopropylidene-L-muco-quercitol
• CAS: 861661-02-1
• 化学式: C₁₂H₁₉ClO₄
• 分子量: 262.733
• InChiKey: BKVOOOALUNXLDO-SQXHDICFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-chloro-5-deoxy-1,2:3,4-di-O-isopropylidene-L-muco-quercitol 在 sodium azide 、 15-冠醚-5 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-L-vibo-quercitol
  参考文献：
  名称：

  Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)-vibo-quercitol

  摘要：

  In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-L-talo-quercitol was designed and synthesized as an analogue of the strong alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate alpha-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxymositols as hexopyranose mimics of biological interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.003
• 作为产物：
  描述：

  (-)-VIBO-栎醇 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 、 吡啶 、 4-二甲氨基吡啶 、 磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 以58%的产率得到3-chloro-3-deoxy-1,2:4,5-di-O-isopropylidene-L-allo-quercitol
  参考文献：
  名称：

  Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)-vibo-quercitol

  摘要：

  In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-L-talo-quercitol was designed and synthesized as an analogue of the strong alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate alpha-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxymositols as hexopyranose mimics of biological interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.003