(R)-pantolactyl tetrahydropyranyl ether | 126214-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (R)-pantolactyl tetrahydropyranyl ether
• 英文别名: (3R)-4,4-dimethyl-3-[(2S)-oxan-2-yl]oxyoxolan-2-one
• CAS: 126214-88-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: PSQDUZLVNUZVHN-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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 、 (R)-pantolactyl tetrahydropyranyl ether 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 2-(2-propenyl)-2-O-(tetrahydropyranyloxy)pantolactone 、 2-(2-propenyl)-2-O-(tetrahydropyranyloxy)pantolactone
  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 、 D-(-)-泛酰内酯 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 (R)-pantolactyl tetrahydropyranyl ether 、 (R)-pantolactyl tetrahydropyranyl ether
  参考文献：
  名称：

  WO2008/48538

  摘要：

  公开号：

文献信息

• WO2008/48538
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.