[(E,3R,4R)-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,4S,6R)-3-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-7-tri(propan-2-yl)silyloxyheptanoate | 216493-92-4

• 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: [(E,3R,4R)-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,4S,6R)-3-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-7-tri(propan-2-yl)silyloxyheptanoate
• CAS: 216493-92-4
• 化学式: C₃₄H₅₉IO₅Si
• 分子量: 702.829
• InChiKey: QLBDLEFOIYUPCZ-QEZNBWCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.98
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(E,3R,4R)-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,4S,6R)-3-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-7-tri(propan-2-yl)silyloxyheptanoate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以94%的产率得到[(E,3R,4R)-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,4S,6R)-7-hydroxy-3-[(4-methoxyphenyl)methoxy]-2,4,6-trimethylheptanoate
  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,3S,4S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentan-3-ol 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 jones reagent 、 2,4,6-三氯苯甲酰氯 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 167.5h， 生成 [(E,3R,4R)-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,4S,6R)-3-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-7-tri(propan-2-yl)silyloxyheptanoate
  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