Toluene-4-sulfonic acid (2S,3S,4R)-5-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester | 183293-42-7

• 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: Toluene-4-sulfonic acid (2S,3S,4R)-5-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester
• 英文别名: [(2S,3S,4R)-5-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-hydroxy-2,4-dimethyl-5-oxopentyl] 4-methylbenzenesulfonate
• CAS: 183293-42-7
• 化学式: C₂₄H₂₉NO₇S
• 分子量: 475.563
• InChiKey: REERJFCKPAQWET-IKLNAOFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2S,3S,4R)-5-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 锂硼氢 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 108.0h， 生成 (2R,4S)-4-[(2'R,4'S,5'S)-2'-(4-methoxyphenyl)-5'-methyl-1',3'-dioxan-4-yl]-2-methylpentan-1-ol
  参考文献：
  名称：

  Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

  摘要：

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.

  DOI：

  10.1021/jo9809433
• 作为产物：
  描述：

  (2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester 在 三氟甲磺酸二丁硼 、 双氧水 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 Toluene-4-sulfonic acid (2S,3S,4R)-5-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester
  参考文献：
  名称：

  Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

  摘要：

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.

  DOI：

  10.1021/jo9809433

文献信息

• Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin
  作者：Ronaldo A. Pilli、Carlos Kleber Z. de Andrade、Carlos Roberto O. Souto、Armin de Meijere

  DOI：10.1021/jo9809433

  日期：1998.10.1

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.