(2R,5S)-5-((R)-1-Methoxycarbonyl-ethyl)-tetrahydro-furan-2-carboxylic acid methyl ester | 523768-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,5S)-5-((R)-1-Methoxycarbonyl-ethyl)-tetrahydro-furan-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,5S)-5-[(2R)-1-methoxy-1-oxopropan-2-yl]oxolane-2-carboxylate
• CAS: 523768-71-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: DVFCPFBPISELHJ-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5S)-5-((R)-1-Methoxycarbonyl-ethyl)-tetrahydro-furan-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(R)-2-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective Syntheses of 2,5-Disubstituted Hydroxyfuran Derivatives as Synthon of Polyether Antibiotics

  摘要：

  Stereoselective syntheses of optically active 2,5-dialkyltetrahydrofurans (8), (11) and (12), which correspond to a central moiety of pamamycin 607, have been achieved on the basis of lactone-ring transformation via a phenonium ion, intramolecular Friedel-Crafts reaction, oxidative decomposition of an aromatic ring and differentiation of two ester groups by a chemical or chemo-enzymatic method.

  DOI：

  10.3987/com-02-s40
• 作为产物：
  描述：

  重氮甲烷 、 (2R,5S)-5-((R)-1-Carboxy-ethyl)-tetrahydro-furan-2-carboxylic acid 以 乙醚 为溶剂， 生成 (2R,5S)-5-((R)-1-Methoxycarbonyl-ethyl)-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective Syntheses of 2,5-Disubstituted Hydroxyfuran Derivatives as Synthon of Polyether Antibiotics

  摘要：

  Stereoselective syntheses of optically active 2,5-dialkyltetrahydrofurans (8), (11) and (12), which correspond to a central moiety of pamamycin 607, have been achieved on the basis of lactone-ring transformation via a phenonium ion, intramolecular Friedel-Crafts reaction, oxidative decomposition of an aromatic ring and differentiation of two ester groups by a chemical or chemo-enzymatic method.

  DOI：

  10.3987/com-02-s40