(+) 3(S) tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxybutyrate | 162971-44-0

• 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: (+) 3(S) tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxybutyrate
• 英文别名: tert-butyl (3S)-4-hydroxy-3-(2-methoxyethoxymethoxy)butanoate
• CAS: 162971-44-0
• 化学式: C₁₂H₂₄O₆
• 分子量: 264.319
• InChiKey: HVBWCJZACTZSGJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+) 3(S) tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxybutyrate 在 重铬酸吡啶 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (-)2(S)-methyl 2-(2-methoxyethoxymethoxy)-3-(tert-butoxycarbonyl)propanoate
  参考文献：
  名称：

  Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.

  摘要：

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.

  DOI：

  10.1016/0957-4166(94)80083-9
• 作为产物：
  描述：

  (+)(R) tert-butyl 3-oxo-4-(p-tolylsulfinyl)butyrate 在 sodium acetate 、 镍 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 57.25h， 生成 (+) 3(S) tert-butyl 3-(2-methoxyethoxymethoxy)-4-hydroxybutyrate
  参考文献：
  名称：

  Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.

  摘要：

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.

  DOI：

  10.1016/0957-4166(94)80083-9

文献信息

• Asymmetric synthesis of (−)-(2E, 4R, 5S, 11R)- cladospolide A, induced by chiral sulfoxides
  作者：Guy Solladié、Antonio Almario

  DOI：10.1016/0957-4166(95)00040-v

  日期：1995.2

  An enantioselective synthesis of (-)-cladospolide in which all the chiral centers are created by asymmetric reduction of beta-ketosulfoxides, is reported.
• Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.
  作者：Guy Solladié、Antonio Almario

  DOI：10.1016/0957-4166(94)80083-9

  日期：1994.9

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.