((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester | 160386-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(2S,3R,6S)-4-bromo-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]acetate
• CAS: 160386-80-1
• 化学式: C₉H₁₃BrO₄
• 分子量: 265.104
• InChiKey: JUCOBIXRLCCXBN-CCGCGBOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 在 2,6-二甲基吡啶 、 lithium hydroxide 、 叔丁基锂 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 生成 4-Hydroxy-2,3-diisopropoxy-4-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-cyclobut-2-enone
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004
• 作为产物：
  描述：

  ((2S,6S)-4-Bromo-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 生成 ((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004

文献信息

• General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D
  作者：Michael P. Winters、Michael Stranberg、Harold W. Moore

  DOI：10.1021/jo00104a004

  日期：1994.12

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.