S-ethyl (2S,3R)-2-t-butyldimethylsiloxy-3-hydroxy-3-methoxycarbonylbutanethioate | 155797-47-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-ethyl (2S,3R)-2-t-butyldimethylsiloxy-3-hydroxy-3-methoxycarbonylbutanethioate
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-ethylsulfanyl-2-hydroxy-2-methyl-4-oxobutanoate
• CAS: 155797-47-0
• 化学式: C₁₄H₂₈O₅SSi
• 分子量: 336.525
• InChiKey: GCMARJXZWBRHLH-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-ethyl (2S,3R)-2-t-butyldimethylsiloxy-3-hydroxy-3-methoxycarbonylbutanethioate 在 镍 氢氟酸 、 氢气 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 (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：

  叔丁基二甲基甲硅烷基氧基乙酰氯 在 吡啶 、 tin(II) trifluoromethanesulfonate 、 (S)-1-propyl-2-<(1,2,3,4-tetrahydroisoquinolinyl)methyl>pyrrolidine 、 三正丁基氟化锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 S-ethyl (2S,3R)-2-t-butyldimethylsiloxy-3-hydroxy-3-methoxycarbonylbutanethioate
  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

文献信息

• Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated
  作者：Shū Kobayashi、Mineko Horibe、Yumi Saito

  DOI：10.1016/s0040-4020(01)85531-9

  日期：——

  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.