(+)-(2S)-methoxy-2-(9E-pentenyl)-4-tetrahydropyrone | 135352-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2S)-methoxy-2-(9E-pentenyl)-4-tetrahydropyrone
• 英文别名: (+)-(2S,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one；(2S)-2-methoxy-2-[(E)-pent-3-enyl]oxan-4-one
• CAS: 135352-09-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: QTWKWQRUYRUEDU-UFFNRZRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(2S)-methoxy-2-(9E-pentenyl)-4-tetrahydropyrone 在 palladium on activated charcoal sodium tetrahydroborate 、 tris(triphenylphosphine)ruthenium(II) chloride 、 氢气 、 三氯化铁 、 L-Selectride 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 、 异丙醇 、 苯 为溶剂， -70.0~25.0 ℃ 、101.33 kPa 条件下， 反应 88.5h， 生成 (+)-(3S,5R)-3-hydroxy-5-decanolide
  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
• 作为产物：
  描述：

  (3S,8E)-1,3-二羟基-8-癸烯-5-酮 在 (C₃H₇)4NRuO₄ 、 N-甲基吗啉氧化物 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 (+)-(2S)-methoxy-2-(9E-pentenyl)-4-tetrahydropyrone
  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

• 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.