(S)-3,3-dimethoxy-2-methylpropan-1-ol | 115757-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3,3-dimethoxy-2-methylpropan-1-ol
• 英文别名: 3,3-dimethoxy-2-methylpropanol；(2S)-3,3-dimethoxy-2-methylpropan-1-ol
• CAS: 115757-27-2
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: GLAXQTDHALEKLY-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (S)-3,3-dimethoxy-2-methylpropan-1-ol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(S)-1-(Benzyloxy)-3,3-dimethoxy-2-methylpropane
  参考文献：
  名称：

  Palladium(II)-catalyzed asymmetric acetalization of alkenes

  摘要：

  The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdCl2 catalyst. The use of 4(S)-isopropyl-, phenyl-, and tert-butyl-2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'S)-acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAlH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of this compound, derived from 4(R)substituted oxazolidinones, served as a building block for synthesizing a 1 beta-methylcarbapenem precursor in high enantiomeric excess. In the acetalization of 3',3'-dideuteriated methacryloyl-4-isopropyloxaiolidinone with MeOH, one D-atom on the terminal olefinic carbon stereoselectively migrated to the chiral center in the product acetal. On the basis of this 1,2-hydride migration and the conformational preference of the methacryloyl moiety, the reaction pathway and the mechanism of the diastereoselection are discussed.

  DOI：

  10.1021/jo00124a032
• 作为产物：
  描述：

  (4R)-3-[(2R)-3,3-dimethoxy-2-methylpropanoyl]-4-phenyl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以66%的产率得到(S)-3,3-dimethoxy-2-methylpropan-1-ol
  参考文献：
  名称：

  Palladium(II)-catalyzed asymmetric acetalization of alkenes

  摘要：

  The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdCl2 catalyst. The use of 4(S)-isopropyl-, phenyl-, and tert-butyl-2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'S)-acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAlH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of this compound, derived from 4(R)substituted oxazolidinones, served as a building block for synthesizing a 1 beta-methylcarbapenem precursor in high enantiomeric excess. In the acetalization of 3',3'-dideuteriated methacryloyl-4-isopropyloxaiolidinone with MeOH, one D-atom on the terminal olefinic carbon stereoselectively migrated to the chiral center in the product acetal. On the basis of this 1,2-hydride migration and the conformational preference of the methacryloyl moiety, the reaction pathway and the mechanism of the diastereoselection are discussed.

  DOI：

  10.1021/jo00124a032

文献信息

• Polymeric Ethyl Glyoxylate in an Asymmetric Aldol Reaction Catalyzed by Diarylprolinol
  作者：Tatsuya Urushima、Yusuke Yasui、Hayato Ishikawa、Yujiro Hayashi

  DOI：10.1021/ol1009812

  日期：2010.7.2

  Diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of commercially available polymeric ethyl glyoxylate, affording γ-ethoxycarbonyl-β-hydroxy aldehydes, versatile synthetic intermediates, in good yield with excellent enantioselectivity.

  发现二芳基脯氨醇是可商购的聚合乙醛酸乙酯直接，对映选择性醛醇缩合反应的有效有机催化剂，以良好的产率和优异的对映选择性提供了γ-乙氧基羰基-β-羟基醛，通用的合成中间体。
• Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of <i>N</i>-Acylthiazolidinethiones
  作者：David A. Evans、Regan J. Thomson

  DOI：10.1021/ja053386s

  日期：2005.8.1

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.
• Enantioselective Total Synthesis of the Osteoclastogenesis Inhibitor (+)-Symbioimine
  作者：Justin Kim、Regan J. Thomson

  DOI：10.1002/anie.200605160

  日期：2007.4.20
• Palladium(II)-catalyzed asymmetric acetalization of alkenes
  作者：Takahiro Hosokawa、Toshio Yamanaka、Motohiro Itotani、Shun-Ichi Murahashi

  DOI：10.1021/jo00124a032

  日期：1995.9

  The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdCl2 catalyst. The use of 4(S)-isopropyl-, phenyl-, and tert-butyl-2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'S)-acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAlH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of this compound, derived from 4(R)substituted oxazolidinones, served as a building block for synthesizing a 1 beta-methylcarbapenem precursor in high enantiomeric excess. In the acetalization of 3',3'-dideuteriated methacryloyl-4-isopropyloxaiolidinone with MeOH, one D-atom on the terminal olefinic carbon stereoselectively migrated to the chiral center in the product acetal. On the basis of this 1,2-hydride migration and the conformational preference of the methacryloyl moiety, the reaction pathway and the mechanism of the diastereoselection are discussed.