(-)-(2R,4S)-4-hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydropyran | 135352-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,4S)-4-hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydropyran
• 英文别名: (-)-(2R,4S,3'E)-4-hydroxy-2-methoxy-2-(3'-pentenyl)-tetrahydropyran；(+)-(2R,4S)-4-Hydroxy-2-methoxy-2-(3E-pentenyl)-tetrahydropyran；(2R,4S)-2-methoxy-2-[(E)-pent-3-enyl]oxan-4-ol
• CAS: 135352-08-8
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: XPPHTOCFYLAQJN-MJKAUQOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2R,4S)-4-hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydropyran 在 tris(triphenylphosphine)ruthenium(II) chloride 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(-)-(2R,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one
  参考文献：
  名称：

  Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones

  摘要：

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.

  DOI：

  10.1016/0040-4020(95)00438-e
• 作为产物：
  描述：

  (3S,8E)-1,3-二羟基-8-癸烯-5-酮 在 lithium bromide 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以5%的产率得到(-)-(2R,4S)-4-hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydropyran
  参考文献：
  名称：

  Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces

  摘要：

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.

  DOI：

  10.1016/s0040-4020(01)86398-5

文献信息

• Verfahren zur stereoselektiven Herstellung von 5-substituierten delta-Lactonen und deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0469480A2

  公开（公告）日：1992-02-05

  Es wird ein Verfahren zur stereoselektiven Herstellung von 5-substituierten 8-Lactonen der Formeln Ia, Ib, Ic und Id wobei R1 für geradkettige oder verzweigte Alkyl- oder Alkenylgruppe oder für Methylhydroxy steht, neue 5-substituierte δ-Lactone und neue Zwischenprodukte, sowie deren Verwendung als Arzneimittel mit Cholesterin-Synthese hemmender Wirkung, Duft- und Geschmackstoffe, beschrieben.

  一种立体选择性制备式 Ia、Ib、Ic 和 Id 的 5-取代 8-内酯的工艺 式中 R1 为直链或支链烷基或烯基或甲基羟基的新 5-取代的 δ-内酯和新中间体，以及它们作为具有胆固醇合成抑制活性的药物、香料和香精的用途。
• Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones
  作者：Joachim Adam、Robert Klein、Susanne Grabley、Peter Hammann

  DOI：10.1016/0040-4020(95)00438-e

  日期：1995.7

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.
• Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces
  作者：Yvonne Romeyke、Martin Keller、Heinz Kluge、Susanne Grabley、Peter Hammann

  DOI：10.1016/s0040-4020(01)86398-5

  日期：1991.1

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.