(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate | 765941-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate
• 英文别名: [(2S,3R,4R,5S,6S)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxy-2,4,6-trimethylheptyl] 4-nitrobenzoate
• CAS: 765941-34-2
• 化学式: C₂₉H₅₃NO₇Si₂
• 分子量: 583.913
• InChiKey: BLFYAYHKMIXSMK-VXOZGMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate 在 咪唑 、 2,6-二甲基吡啶 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,4R,5S,6R)-1,5-bis(tert-butyldimethylsilyloxy)-7-iodo-2,4,6-trimethyl-3-triethylsilyloxyheptane
  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) 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 四氧化锇 、 锂硼氢 、 N-甲基吲哚酮 、 2,6-二叔丁基-4-甲基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 39.67h， 生成 (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-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

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.