(Z)-(S)-1-Methoxy-1,3-bis-triethylsilanyloxy-but-1-ene | 122553-23-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-(S)-1-Methoxy-1,3-bis-triethylsilanyloxy-but-1-ene
• 英文别名: triethyl-[(Z,3S)-1-methoxy-3-triethylsilyloxybut-1-enoxy]silane
• CAS: 122553-23-5
• 化学式: C₁₇H₃₈O₃Si₂
• 分子量: 346.658
• InChiKey: SICYJCPPBMMVCE-SCDSTIRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-苄氧基丙醛 、 (Z)-(S)-1-Methoxy-1,3-bis-triethylsilanyloxy-but-1-ene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4R)-4-Benzyloxy-3-hydroxy-2-((S)-1-hydroxy-ethyl)-pentanoic acid methyl ester
  参考文献：
  名称：

  Diastereofacial Selection in Titanium Tetrachloride-Promoted Aldol Reactions with the Silyl Ketene Acetal of Methyl (R)-3-Hydroxybutanoate

  摘要：

  与在与手性酯的二锂烯醇盐反应中观察到的 "同步 "选择相反，标题反应显示出高度的 "反 "非对映选择。讨论了 "反 "立体选择的机理依据。

  DOI：

  10.1246/cl.1990.1931

文献信息

• A novel, double-asymmetric aldol approach to the synthesis of a 1β-methyl carbapenem antibiotic precursor
  作者：Fumiyuki Shirai、Takeshi Nakai

  DOI：10.1016/s0040-4039(00)82373-4

  日期：1988.1

  A novel synthetic approach to the 1β-methyl carbapenem key precursor is described which involves the chelation-controlled double-asymmetric aldol reaction as the key step.

  描述了一种新型的合成1β-甲基碳青霉烯关键前体的方法，该方法涉及螯合控制的双不对称羟醛反应作为关键步骤。
• Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate
  作者：Jin-Hua Gu、Masahiro Terada、Koichi Mikami、Takeshi Nakai

  DOI：10.1016/s0040-4039(00)91648-4

  日期：1992.3

  The Eu(III)-catalyzed reaction of alpha-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both ''anti'' diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.
• SHIRAI, FUMIYUKI;GU, JIN-HUA;NAKAI, TAKESHI, CHEM. LETT.,(1990) N0, C. 1931-1934
  作者：SHIRAI, FUMIYUKI、GU, JIN-HUA、NAKAI, TAKESHI

  DOI：——

  日期：——
• Diastereofacial Selection in Titanium Tetrachloride-Promoted Aldol Reactions with the Silyl Ketene Acetal of Methyl (<i>R</i>)-3-Hydroxybutanoate
  作者：Fumiyuki Shirai、Jin-Hua Gu、Takeshi Nakai

  DOI：10.1246/cl.1990.1931

  日期：1990.10

  The title reaction is shown to exhibit a high level of “anti” diastereofacial selection, in contrast to the “syn” selection observed for the reaction with the dilithium enolate of the chiral ester. Mechanistic grounds for the “anti” stereoselection are discussed.

  与在与手性酯的二锂烯醇盐反应中观察到的 "同步 "选择相反，标题反应显示出高度的 "反 "非对映选择。讨论了 "反 "立体选择的机理依据。