5-(E)-eno-3-hydroxy-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose | 471923-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(E)-eno-3-hydroxy-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
• 英文别名: (E)-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-eno-1,4-furanos-7-ulose；(E)-4-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]but-3-en-2-one
• CAS: 471923-35-0
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: JMYPIBRZDWKJAB-DTYMUTQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(E)-eno-3-hydroxy-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose 在 对甲苯磺酸 、 水 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以40%的产率得到5-(acetylmethyl)-furfural
  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
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium periodate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 5-(E)-eno-3-hydroxy-1,2-O-isopropylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
  参考文献：
  名称：

  为（1的合成方法Chiron公司小号，2 - [R，5 - [R 7小号）-2-羟基-外型-brevicomin

  摘要：

  （1级小号，2 - [R，5 - [R 7小号）-2-羟基-外型-brevicomin ENT - 1从1,2-合成; 5,6-二- ö异亚丙基d葡萄糖在七个步骤。我们合成过程中的关键反应是在D-葡萄糖衍生物6的1,2-丙酮化物的酸介导的乙缩醛交换下形成双环缩酮7。

  DOI：

  10.1016/j.tetasy.2006.02.020