(5S,6R)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-5-methyl-5,6-dihydropyran-2-one | 765941-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5S,6R)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-5-methyl-5,6-dihydropyran-2-one
• 英文别名: (2R,3S)-2-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-3-methyl-2,3-dihydropyran-6-one
• CAS: 765941-21-7
• 化学式: C₁₅H₂₈O₃Si
• 分子量: 284.471
• InChiKey: XUGBVWFLTIUEFC-SGMGOOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (5S,6R)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-5-methyl-5,6-dihydropyran-2-one 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 以72%的产率得到(3S,4S,5S,6S)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-3,4-dihydroxy-5-methyltetrahydropyran-2-one
  参考文献：
  名称：

  Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones:  A Novel Protocol for the Stereoselective Synthesis of C₁−C₈ and C₁₅−C₂₁ Subunits of (+)-Discodermolide

  摘要：

  Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.

  DOI：

  10.1021/jo0492416
• 作为产物：
  描述：

  (2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (5S,6R)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-5-methyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones:  A Novel Protocol for the Stereoselective Synthesis of C₁−C₈ and C₁₅−C₂₁ Subunits of (+)-Discodermolide

  摘要：

  Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.

  DOI：

  10.1021/jo0492416

文献信息

• Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones:  A Novel Protocol for the Stereoselective Synthesis of C₁−C₈ and C₁₅−C₂₁ Subunits of (+)-Discodermolide
  作者：P. Veeraraghavan Ramachandran、Bodhuri Prabhudas、J. Subash Chandra、M. Venkat Ram Reddy

  DOI：10.1021/jo0492416

  日期：2004.9.1

  Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.