(2R,3R)-3-t-butyldimethylsiloxy-2-hydroxy-2-methyl-γ-butyrolactone | 160114-65-8

• 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: (2R,3R)-3-t-butyldimethylsiloxy-2-hydroxy-2-methyl-γ-butyrolactone
• CAS: 160114-65-8
• 化学式: C₁₁H₂₂O₄Si
• 分子量: 246.379
• InChiKey: MHVLADNITIAQAI-LDYMZIIASA-N

物化性质

• 沸点：
  296.4±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-t-butyldimethylsiloxy-2-hydroxy-2-methyl-γ-butyrolactone 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以24.6 mg的产率得到(3R,4R)-二氢-3,4-二羟基-3-甲基-2(3H)-呋喃酮
  参考文献：
  名称：

  Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated

  摘要：

  Diastereo- and enantioselective synthesis of both diastereomers, including the alpha-alkoxy-beta-hydroxy-beta-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of a-alkoxy silyl enol ethers with alpha-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-a,p-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.

  DOI：

  10.1016/s0040-4020(01)85531-9
• 作为产物：
  描述：

  (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene 在 镍 tin(II) trifluoromethanesulfonate 、 (S)-1-propyl-2-<(1,2,3,4-tetrahydroisoquinolinyl)methyl>pyrrolidine 、 氢气 、 三正丁基氟化锡 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 25.0h， 生成 (2R,3R)-3-t-butyldimethylsiloxy-2-hydroxy-2-methyl-γ-butyrolactone
  参考文献：
  名称：

  Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated

  摘要：

  Diastereo- and enantioselective synthesis of both diastereomers, including the alpha-alkoxy-beta-hydroxy-beta-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of a-alkoxy silyl enol ethers with alpha-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-a,p-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.

  DOI：

  10.1016/s0040-4020(01)85531-9