(2R,3R,4S,5R,E)-5-Acetoxy-3,4-dihydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone | 146384-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2R,3R,4S,5R,E)-5-Acetoxy-3,4-dihydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone
• CAS: 146384-01-2
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: UCTQNAGWXUBXQR-QLTPLPSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5R,E)-5-Acetoxy-3,4-dihydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(-)-(2R,3R,4S,5R,E)-3,5-Diacetoxy-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017
• 作为产物：
  描述：

  (+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate 在 吡啶 、 lithium tetrafluoroborate 、 水 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 129.33h， 生成 (2R,3R,4S,5R,E)-5-Acetoxy-3,4-dihydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017