ethyl 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate | 136838-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: ethyl 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate
• 英文别名: ethyl (1S,2R,6R,8R)-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecane-10-carboxylate
• CAS: 136838-97-6；136839-02-6；136839-12-8；136839-17-3
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: IVWLOICSVKKFIT-WGARXNEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate 、 碘代醋酸乙酯 在 lithium diisopropyl amide 作用下， 生成 ethyl 3,6-anhydro-6α-(carboxyethyl)-5,7-dideoxy-1,2-O-isopropylidene-α-D-xylo-nonofuranuronate 、 ethyl 3,6-anhydro-6β-(carboxyethyl)-5,7-dideoxy-1,2-O-isopropylidene-α-D-xylo-nonofuranuronate
  参考文献：
  名称：

  Total synthesis of griseolic acid derivatives from D-glucose

  摘要：

  Griseolic acid, 1, is a potent nonselective cyclic nucleotide-phosphodiesterase inhibitor isolated from Streptomyces Griseoaurantiacus. Recently, preparation of several griseolic acid derivatives, including 3, has been reported. We have completed the chiral total synthesis of several griseolic acid derivatives. Here, we report on total syntheses of two cis-fused 4',5'-dihydro-7'-deoxy griseolic acid derivatives, 4 and 5, from D-glucose.

  DOI：

  10.1021/jo00024a022
• 作为产物：
  描述：

  (Z)-ethyl 5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-eno-1,4-furanuronate 在 palladium on activated charcoal 氢气 、 溴 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， -78.0 ℃ 、413.69 kPa 条件下， 反应 2.5h， 生成 ethyl 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate
  参考文献：
  名称：

  Total synthesis of griseolic acid derivatives from D-glucose

  摘要：

  Griseolic acid, 1, is a potent nonselective cyclic nucleotide-phosphodiesterase inhibitor isolated from Streptomyces Griseoaurantiacus. Recently, preparation of several griseolic acid derivatives, including 3, has been reported. We have completed the chiral total synthesis of several griseolic acid derivatives. Here, we report on total syntheses of two cis-fused 4',5'-dihydro-7'-deoxy griseolic acid derivatives, 4 and 5, from D-glucose.

  DOI：

  10.1021/jo00024a022