[(2S,3R,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentyl] 4-methylbenzenesulfonate | 183293-43-8

• 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,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentyl] 4-methylbenzenesulfonate
• CAS: 183293-43-8
• 化学式: C₂₀H₃₆O₅SSi
• 分子量: 416.654
• InChiKey: HAUXFCSVIMWWQP-LNLFQRSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentyl] 4-methylbenzenesulfonate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 105.0h， 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,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 11.5h， 生成 [(2S,3R,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentyl] 4-methylbenzenesulfonate
  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