(3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-(hydroxymethyl)-γ-butyrolactone | 159685-34-4

• 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-(hydroxymethyl)-γ-butyrolactone
• 英文别名: (4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 159685-34-4
• 化学式: C₁₁H₂₂O₄Si
• 分子量: 246.379
• InChiKey: XRQGUZINQATRRR-BDAKNGLRSA-N

物化性质

• 沸点：
  327.1±27.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-(hydroxymethyl)-γ-butyrolactone 在 咪唑 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 乙醚 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 (-)-(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 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 (3R,4S)-3-<(tert-Butyldimethylsilyl)oxy>-4-(hydroxymethyl)-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

• Stereoselective Oxylactonization. Preparation of 2-Deoxy-DL-ribono-1,4-lactone Derivatives from 3-Silyloxy-4-alkenamides
  作者：Yuh-ichiro Ichikawa、Tetsuo Miwa、Koichi Narasaka

  DOI：10.1246/bcsj.58.3309

  日期：1985.11

  The oxylactonization of 3-silyloxy-4-alkenamides proceeds stereoselectively by treatment with m-chloroperbenzoic acid to give the corresponding 2-deoxy-DL-ribono-1,4-lactone derivatives.

  3-甲硅烷氧基-4-链烯酰胺的氧基内酯化通过用间氯过苯甲酸处理而立体选择性地进行，得到相应的2-脱氧-DL-核糖-1,4-内酯衍生物。
• 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)].