endo-3,5-anhydro-6,8-dideoxy-1,2-O-(R)-trichloroethylidene-a-D-xylo-1,4-furano-7-ulose di-O-methylacetal | 1402434-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-3,5-anhydro-6,8-dideoxy-1,2-O-(R)-trichloroethylidene-a-D-xylo-1,4-furano-7-ulose di-O-methylacetal
• CAS: 1402434-40-5
• 化学式: C₁₂H₁₇Cl₃O₆
• 分子量: 363.622
• InChiKey: UDRVGRHJMREVOR-HDBWYCHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲醇 、 5-(E)-eno-3-hydroxy-1,2-O-(R)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose 在 对甲苯磺酸 作用下， 反应 5.0h， 以45%的产率得到exo-3,5-anhydro-6,8-dideoxy-1,2-O-(R)-trichloroethylidene-a-D-xylo-1,4-furano-7-ulose di-O-methylacetal
  参考文献：
  名称：

  Acid promoted intramolecular formation of 3,5-anhydro-1,4-furano-7-ulose derivatives via the Wittig-cyclization procedure and their antimicrobial properties

  摘要：

  We report a convenient method for the synthesis of 3,5-anhydrofuranose derivatives. Formation of the 3,5-anhydro (oxetane) rings was achieved by the Wittig-cyclization procedure under acid promoted conditions starting from 5(E)-eno-1,4-furano-7-ulose derivatives (1, 4, and 7). Unprotected hydroxyl groups on C-3 of the furanose rings added intramolecularly to the acyclic double bond under very mild acidic conditions in methanol to form the stereoisomeric 3,5-anhydro derivatives in good yields. The products (2, 3, 5, 6, and 8) were found to exhibit antibacterial properties. The reaction was found to be strongly solvent dependent as use of methanol instead of chloroform afforded 5-acetylmethyl-furfural 9 as a major product instead of the expected oxetane. All of the synthesized compounds were tested for antimicrobial activity against Staphylococcus aureus ATCC6538-P, Bacillus subtilis ATCC 6633, Salmonella typhimurium CCM 5445, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 12228, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae CCM 2318, and Candida albicans ATCC 10239 and exhibited a range of activities against selected microorganisms.

  DOI：

  10.1007/s00044-012-0218-4