(2S,5R)-5-[(S)-tert-Butoxycarbonyl-(tetrahydro-pyran-2-yloxy)-methyl]-tetrahydro-furan-2-carboxylic acid methyl ester | 141039-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,5R)-5-[(S)-tert-Butoxycarbonyl-(tetrahydro-pyran-2-yloxy)-methyl]-tetrahydro-furan-2-carboxylic acid methyl ester
• 英文别名: (2S,5R)-5-[(R)-tert-Butoxycarbonyl-(tetrahydro-pyran-2-yloxy)-methyl]-tetrahydro-furan-2-carboxylic acid methyl ester
• CAS: 141039-63-6
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: NWLUYAGFSBBSIK-QNMSZWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-5-[(S)-tert-Butoxycarbonyl-(tetrahydro-pyran-2-yloxy)-methyl]-tetrahydro-furan-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (S)-2-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-2-(tetrahydro-pyran-2-yloxy)-ethanol
  参考文献：
  名称：

  Development of tetrahydrofuran chiral synthons by enzymatic approach: Improved synthesis of a strong agonist of platelet activating factor

  摘要：

  Bicyclic meso diester 7 was found to undergo enantioselective hydrolysis with PLE (pig liver esterase) generating the chiral monoester 8 in excellent yield with high enantiomeric excess. The chiral monoester 8 was successfully utilized in the improved synthesis of 1R-cis-THF derivative (1), a strong agonist of PAF which we previously developed.

  DOI：

  10.1016/s0040-4039(00)91866-5
• 作为产物：
  描述：

  (2S,5R)-5-tert-Butoxyoxalyl-tetrahydro-furan-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2S,5R)-5-[(S)-tert-Butoxycarbonyl-(tetrahydro-pyran-2-yloxy)-methyl]-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Development of tetrahydrofuran chiral synthons by enzymatic approach: Improved synthesis of a strong agonist of platelet activating factor

  摘要：

  Bicyclic meso diester 7 was found to undergo enantioselective hydrolysis with PLE (pig liver esterase) generating the chiral monoester 8 in excellent yield with high enantiomeric excess. The chiral monoester 8 was successfully utilized in the improved synthesis of 1R-cis-THF derivative (1), a strong agonist of PAF which we previously developed.

  DOI：

  10.1016/s0040-4039(00)91866-5