(S)-methyl 2-hydroxy-4-methylvaleryl tetrahydropyranyl ether | 131489-86-6

• 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: (S)-methyl 2-hydroxy-4-methylvaleryl tetrahydropyranyl ether
• 英文别名: methyl (2S)-4-methyl-2-[(2R)-oxan-2-yl]oxypentanoate
• CAS: 131489-86-6
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: ULDDWJVMUKGMGS-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 (S)-methyl 2-hydroxy-4-methylvaleryl tetrahydropyranyl ether 在 lithium diisopropyl amide 作用下， 生成 methyl 2-(2-methylpropyl)-2-(tetrahydropyranyloxy)pent-4-enoate 、 methyl 2-(2-methylpropyl)-2-(tetrahydropyranyloxy)pent-4-enoate
  参考文献：
  名称：

  Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates

  摘要：

  A concise approach for the rapid synthesis of enantiomerically pure alpha-alkylated derivatives of lactate esters and of other enantiomerically pure alpha-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other alpha-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.

  DOI：

  10.1021/jo00003a035
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (S)-2-羟基-4-甲基戊酸甲酯 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到(S)-methyl 2-hydroxy-4-methylvaleryl tetrahydropyranyl ether
  参考文献：
  名称：

  Enantiomerically pure acetals in organic synthesis. 1. Chromatographic separability of furanoside and pyranoside acetals derived from .alpha.-hydroxy esters

  摘要：

  A general chromatographic separation of diastereomeric furanoside and pyranoside acetals derived from alpha-hydroxy esters is described. Application of this separation methodology is made to rapid syntheses of the diastereomers of (S)-methyl lactyl 4-deoxy-beta-erythro-pentopyranoside.

  DOI：

  10.1021/jo00003a034

文献信息

• Enantiomerically pure acetals in organic synthesis. 1. Chromatographic separability of furanoside and pyranoside acetals derived from .alpha.-hydroxy esters
  作者：Eugene A. Mash、Jeffrey B. Arterburn、James A. Fryling、Susan H. Mitchell

  DOI：10.1021/jo00003a034

  日期：1991.2

  A general chromatographic separation of diastereomeric furanoside and pyranoside acetals derived from alpha-hydroxy esters is described. Application of this separation methodology is made to rapid syntheses of the diastereomers of (S)-methyl lactyl 4-deoxy-beta-erythro-pentopyranoside.
• Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates
  作者：Eugene A. Mash、James A. Fryling

  DOI：10.1021/jo00003a035

  日期：1991.2

  A concise approach for the rapid synthesis of enantiomerically pure alpha-alkylated derivatives of lactate esters and of other enantiomerically pure alpha-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other alpha-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.