(3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone | 159685-38-8

• 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: (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone
• 英文别名: (4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyloxolan-2-one
• CAS: 159685-38-8
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: MUYHKGSTIOXKLP-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以89%的产率得到(-)-(4R,5S)-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008
• 作为产物：
  描述：

  (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 50.0h， 生成 (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008

文献信息

• New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00103a008

  日期：1994.12

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].