(3S,4S,5S,6S)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-3,4-dihydroxy-5-methyltetrahydropyran-2-one | 765941-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,5S,6S)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-3,4-dihydroxy-5-methyltetrahydropyran-2-one
• 英文别名: (3S,4S,5S,6S)-6-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-3,4-dihydroxy-5-methyloxan-2-one
• CAS: 765941-23-9
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: IMRHNOILHSSPAP-VLJOUNFMSA-N

物化性质

• 沸点：
  377.8±11.0 °C(predicted)
• 密度：
  1.057±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S,6S)-6-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-3,4-dihydroxy-5-methyltetrahydropyran-2-one 在 吡啶 、 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 锂硼氢 、 2,6-二叔丁基-4-甲基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 29.67h， 生成 (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-triethylsilyloxy-2,4,6-trimethylheptyl p-nitrobenzoate
  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) 四氧化锇 、 N-甲基吲哚酮 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 10.0h， 生成 (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

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.