ethyl 3,6-anhydro-6α-carbethoxy-5,7-dideoxy-1,2-O-isopropylidene-β-L-lyxo-nonofuranuronate | 136839-13-9

• 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-6α-carbethoxy-5,7-dideoxy-1,2-O-isopropylidene-β-L-lyxo-nonofuranuronate
• 英文别名: ethyl (1R,2R,6R,8S,10R)-10-(2-ethoxy-2-oxoethyl)-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecane-10-carboxylate
• CAS: 136839-13-9
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: MQTHRABSLZFZNO-COOPQGGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,6-anhydro-6α-carbethoxy-5,7-dideoxy-1,2-O-isopropylidene-β-L-lyxo-nonofuranuronate 在 三氟甲磺酸三甲基硅酯 、 硫酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 (2R,3aS,5R,6R,6aR)-6-Acetoxy-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-ethoxycarbonylmethyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester
  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：

  ethyl 3,6-anhydro-5-deoxy-1,2-O-isopropylidene-β-L-lyxo-heptofuranuronate 、 碘代醋酸乙酯 在 lithium diisopropyl amide 作用下， 生成 ethyl 3,6-anhydro-6α-carbethoxy-5,7-dideoxy-1,2-O-isopropylidene-β-L-lyxo-nonofuranuronate 、 ethyl 3,6-anhydro-6β-carbethoxy-5,7-dideoxy-1,2-O-isopropylidene-β-L-lyxo-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