(2E,4S,5S,6R,7R,8E)-p-tolyl 7-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4,6,8-trimethyl-9-(2-methyloxazol-4-yl)nona-2,8-dienoate | 1403986-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (2E,4S,5S,6R,7R,8E)-p-tolyl 7-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4,6,8-trimethyl-9-(2-methyloxazol-4-yl)nona-2,8-dienoate
• CAS: 1403986-86-6
• 化学式: C₂₉H₄₃NO₅Si
• 分子量: 513.75
• InChiKey: DUAOMINBLNKNKU-VJRBKWGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  81.79
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E,4S,5S,6R,7R,8E)-p-tolyl 7-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4,6,8-trimethyl-9-(2-methyloxazol-4-yl)nona-2,8-dienoate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以71%的产率得到4-methylphenyl 2-((2S,3R,4S,5R,6R)-tetrahydro-4-hydroxy-3,5-dimethyl-6-((E)-1-(2-methyloxazol-4-yl)prop-1-en-2-yl)-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Synthesis of the C20–C32 Tetrahydropyran Core of the Phorboxazoles and the C22 Epimer via a Stereodivergent Michael Reaction

  摘要：

  A stereoselective synthesis of the C20-C32 tetrahydropyran core of the phorboxazoles has been achieved in only seven steps and in a 31% overall yield. The C22 epimer was also synthesized. The key step was a silyl ether deprotection/oxy-Michael cyclization. When this step was conducted under Bronsted acid conditions, the C20-C32 core was formed with the desired 2,6-cis-stereochemistry. However, when the silyl ether deprotection/oxy-Michael cyclization was conducted under fluoride conditions buffered with acetic acid, the C22 epimer of the core was the sole product.

  DOI：

  10.1021/ol3026523
• 作为产物：
  描述：

  在 Hoveyda-Grubbs catalyst second generation 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 42.25h， 生成 (2E,4S,5S,6R,7R,8E)-p-tolyl 7-((tert-butyldimethylsilyl)oxy)-5-hydroxy-4,6,8-trimethyl-9-(2-methyloxazol-4-yl)nona-2,8-dienoate
  参考文献：
  名称：

  Synthesis of the C20–C32 Tetrahydropyran Core of the Phorboxazoles and the C22 Epimer via a Stereodivergent Michael Reaction

  摘要：

  A stereoselective synthesis of the C20-C32 tetrahydropyran core of the phorboxazoles has been achieved in only seven steps and in a 31% overall yield. The C22 epimer was also synthesized. The key step was a silyl ether deprotection/oxy-Michael cyclization. When this step was conducted under Bronsted acid conditions, the C20-C32 core was formed with the desired 2,6-cis-stereochemistry. However, when the silyl ether deprotection/oxy-Michael cyclization was conducted under fluoride conditions buffered with acetic acid, the C22 epimer of the core was the sole product.

  DOI：

  10.1021/ol3026523