(S)-3,3-Dimethoxy-3-methylpropanoic acid | 172265-79-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3,3-Dimethoxy-3-methylpropanoic acid
• 英文别名: (S)-3,3-dimethoxy-2-methylpropanoic acid；(2S)-3,3-dimethoxy-2-methylpropanoic acid
• CAS: 172265-79-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: OEFYPYDLUNTURE-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  重氮甲烷 、 (S)-3,3-Dimethoxy-3-methylpropanoic acid 以65%的产率得到methyl (2S)-3,3-dimethoxy-2-methylpropanoate
  参考文献：
  名称：

  Palladium(II)-catalysed asymmetric acetalization of alkenes

  摘要：

  以 4-叔丁基恶唑烷-2-酮为手性助剂的甲基丙烯酰胺在 PdCl2 催化剂存在下与甲醇反应，生成 95% 非对映异构过量的相应缩醛，去除助剂后形成手性缩醛。

  DOI：

  10.1039/c39930000117
• 作为产物：
  描述：

  (4S,2'S)-3-(3',3'-dimethoxy-2'-methylpropionyl)-4-tert-butyloxazolidin-2-one 在 过氧化氢,锂盐(1:1) 作用下， 生成 (S)-3,3-Dimethoxy-3-methylpropanoic acid
  参考文献：
  名称：

  Palladium(II)-catalysed asymmetric acetalization of alkenes

  摘要：

  以 4-叔丁基恶唑烷-2-酮为手性助剂的甲基丙烯酰胺在 PdCl2 催化剂存在下与甲醇反应，生成 95% 非对映异构过量的相应缩醛，去除助剂后形成手性缩醛。

  DOI：

  10.1039/c39930000117

文献信息

• Palladium(II)-catalysed asymmetric acetalization of alkenes
  作者：Takahiro Hosokawa、Toshio Yamanaka、Shun-Ichi Murahashi

  DOI：10.1039/c39930000117

  日期：——

  Methacrylamide bearing 4-tert-butyloxazolidin-2-one as a chiral auxiliary reacts with methanol in the presence of PdCl2 catalyst to give the corresponding acetal in 95% diastereoisomeric excess, and removal of the auxiliary results in the formation of chiral acetals.

  以 4-叔丁基恶唑烷-2-酮为手性助剂的甲基丙烯酰胺在 PdCl2 催化剂存在下与甲醇反应，生成 95% 非对映异构过量的相应缩醛，去除助剂后形成手性缩醛。
• 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.
• 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.