menthyl 2(S),3-dihydroxy-2-methylpropanoate | 147501-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: menthyl 2(S),3-dihydroxy-2-methylpropanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-2,3-dihydroxy-2-methylpropanoate
• CAS: 147501-84-6
• 化学式: C₁₄H₂₆O₄
• 分子量: 258.358
• InChiKey: MXBRJUCSKQZLEF-CZXHOFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  menthyl 2(S),3-dihydroxy-2-methylpropanoate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (S)-2,3-dihydroxy-2-methyl-propionic acid
  参考文献：
  名称：

  Preparation of 2(R) and 2(S) methyl-2-methylglycerates

  摘要：

  Optically pure samples of both enantiomers of methyl 2,3-dihydroxy-2-methylpropanoate were prepared by a chromatographic separation of their (-)-menthyl esters followed by hydrolysis and methylation. Their absolute stereochemistries were established by conversion into their 3-0-acetyl derivatives, compounds of established configuration. NMR and CG-MS methods of determining the optical purities of the diols are described.

  DOI：

  10.1016/s0957-4166(00)86020-6
• 作为产物：
  描述：

  L-薄荷醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 48.0h， 生成 menthyl 2(S),3-dihydroxy-2-methylpropanoate
  参考文献：
  名称：

  Preparation of 2(R) and 2(S) methyl-2-methylglycerates

  摘要：

  Optically pure samples of both enantiomers of methyl 2,3-dihydroxy-2-methylpropanoate were prepared by a chromatographic separation of their (-)-menthyl esters followed by hydrolysis and methylation. Their absolute stereochemistries were established by conversion into their 3-0-acetyl derivatives, compounds of established configuration. NMR and CG-MS methods of determining the optical purities of the diols are described.

  DOI：

  10.1016/s0957-4166(00)86020-6

文献信息

• Synthesis and biological evaluation of 1α-hydroxy-25(R and S)-25,26-Epoxy-23-yne vitamin D3 and of 1α,25(R and S),26-Trihydroxy-23-yne vitamin D3
  作者：Yusheng Wu、Xu-yang Zhao、P. De Clercq、M. Vandewalle、R. Bouillon、A. Verstuyf

  DOI：10.1016/s0960-894x(97)00138-8

  日期：1997.1

  The synthesis of both 1 alpha-hydroxy-25(R and S)-25,26-epoxy-23-yne vitamin D-3 and of both 1 alpha,2S(R and S),26-trihydroxy-23-yne vitamin D-3 is described. Biological evaluation includes the study of calcemic effect, receptor binding and cell differentiation. (C) 1997 Published by Elsevier Science Ltd.
• Preparation of 2(R) and 2(S) methyl-2-methylglycerates
  作者：Juan B. Rodríguez、Sanford P. Markey、Herman Ziffer

  DOI：10.1016/s0957-4166(00)86020-6

  日期：1993.1

  Optically pure samples of both enantiomers of methyl 2,3-dihydroxy-2-methylpropanoate were prepared by a chromatographic separation of their (-)-menthyl esters followed by hydrolysis and methylation. Their absolute stereochemistries were established by conversion into their 3-0-acetyl derivatives, compounds of established configuration. NMR and CG-MS methods of determining the optical purities of the diols are described.