(R)-methyl 2-(benzyloxy)-3,3-dimethoxy-2-methylpropanoate | 138834-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-methyl 2-(benzyloxy)-3,3-dimethoxy-2-methylpropanoate
• 英文别名: methyl (2R)-3,3-dimethoxy-2-methyl-2-phenylmethoxypropanoate
• CAS: 138834-92-1
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: VCJCRHNPBIKIAX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(benzyloxy)-3,3-dimethoxy-2-methylpropanoate 在 palladium on activated charcoal 、 (CF3SO3)2 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (S)-2,2,4-trimethyl-4-(dimethoxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Optically active quaternary carbon centers from the photoaddition of chromium-alkoxycarbene complexes and optically active thiazolines

  摘要：

  The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active beta-lactam penam derivatives in fair to good yield and with high diastereoselectivity. In most cases alcoholosis of the beta-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states-alkane, alkoxy, aldehyde, and ester. The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.

  DOI：

  10.1021/jo00031a025
• 作为产物：
  描述：

  (3S,5R,6S)-6-(benzyloxy)-3-isopropyl-6-methylpenam 在 盐酸 、 碘 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (R)-methyl 2-(benzyloxy)-3,3-dimethoxy-2-methylpropanoate
  参考文献：
  名称：

  Optically active quaternary carbon centers from the photoaddition of chromium-alkoxycarbene complexes and optically active thiazolines

  摘要：

  The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active beta-lactam penam derivatives in fair to good yield and with high diastereoselectivity. In most cases alcoholosis of the beta-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states-alkane, alkoxy, aldehyde, and ester. The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.

  DOI：

  10.1021/jo00031a025

文献信息

• Optically active quaternary carbon centers from the photoaddition of chromium-alkoxycarbene complexes and optically active thiazolines
  作者：Douglas K. Thompson、Naoki Suzuki、Louis S. Hegedus、Yoshitaka Satoh

  DOI：10.1021/jo00031a025

  日期：1992.2

  The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active beta-lactam penam derivatives in fair to good yield and with high diastereoselectivity. In most cases alcoholosis of the beta-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states-alkane, alkoxy, aldehyde, and ester. The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.