5-deoxy-1,2-O-isopropylidene-3-O-methyl-5-oximino-α-D-xylofuranose | 32795-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-1,2-O-isopropylidene-3-O-methyl-5-oximino-α-D-xylofuranose
• CAS: 32795-34-9
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: PYSXIYUDNJEPQX-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.51
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-deoxy-1,2-O-isopropylidene-3-O-methyl-5-oximino-α-D-xylofuranose 在 N-氯代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Diastereoselective Synthesis and Antifungal Activity of Glycosyl Isoxazolines

  摘要：

  Glycosyl nitrile oxides, generated in situ by reaction of glycosyl oximes (3a, 3b, 4) with N-chlorosuccinimide and DBU, on 1,3-dipolar cycloaddition with substituted alkenes resulted in glycosyl isoxazolines (5, 7-28) in diastereoselective manner. The extent of diastereoselection varies with the nature of substituents both in sugar and alkenes. The compounds synthesized were screened in vitro against many fungi wherein two of the compounds (12, 23) showed significant inhibition against Sporothrix schenckii, Trychophyton mentagrophytes, and Cryptococcus neoformans with MIC of 12.5 and 6.25 mug/mL, respectively.

  DOI：

  10.1081/car-200037331
• 作为产物：
  描述：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 在 吡啶 、 4-二甲氨基吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-deoxy-1,2-O-isopropylidene-3-O-methyl-5-oximino-α-D-xylofuranose
  参考文献：
  名称：

  Diastereoselective Synthesis and Antifungal Activity of Glycosyl Isoxazolines

  摘要：

  Glycosyl nitrile oxides, generated in situ by reaction of glycosyl oximes (3a, 3b, 4) with N-chlorosuccinimide and DBU, on 1,3-dipolar cycloaddition with substituted alkenes resulted in glycosyl isoxazolines (5, 7-28) in diastereoselective manner. The extent of diastereoselection varies with the nature of substituents both in sugar and alkenes. The compounds synthesized were screened in vitro against many fungi wherein two of the compounds (12, 23) showed significant inhibition against Sporothrix schenckii, Trychophyton mentagrophytes, and Cryptococcus neoformans with MIC of 12.5 and 6.25 mug/mL, respectively.

  DOI：

  10.1081/car-200037331