2-(N-(benzyl)mesitylsulfonamido)-1-phenylpropyl 3-hydroxy-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enoate | 1247879-97-5

• 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: 2-(N-(benzyl)mesitylsulfonamido)-1-phenylpropyl 3-hydroxy-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enoate
• 英文别名: [(1S,2R)-2-[benzyl-(2,4,6-trimethylphenyl)sulfonylamino]-1-phenylpropyl] (E,2S,3R)-3-hydroxy-2,4-dimethyl-5-(2-methyl-1,3-oxazol-4-yl)pent-4-enoate
• CAS: 1247879-97-5
• 化学式: C₃₆H₄₂N₂O₆S
• 分子量: 630.805
• InChiKey: ZXPHOQMERHDYDN-NEVTXKSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(N-(benzyl)mesitylsulfonamido)-1-phenylpropyl 3-hydroxy-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enoate 在 2,6-二甲基吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成
  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：

  2-(N-benzylmesitylsulfonamido)-1-phenyl-1-propyl propionate 、 (E)-2-methyl-3-(2-methyloxazol-5-yl)acrylaldehyde 、 双环己基(三氟甲烷磺酰氧基)硼烷 在 三乙胺 、 甲醇 、 双氧水 作用下， 以 正己烷 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-(N-(benzyl)mesitylsulfonamido)-1-phenylpropyl 3-hydroxy-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enoate 、 2-(N-(benzyl)-N-mesitylsulfonamido)-1-phenylpropyl 3-hydroxy-2,4-dimethyl-5-(2-methyloxazol-4-yl)pent-4-enoate
  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