(3S)-3-(6-methoxy-2-naphthyl)-4-methyl-2-oxo-3-[(trimethylsilyl)oxy]pentyl p-toluenesulfonate | 727723-03-7

• 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: (3S)-3-(6-methoxy-2-naphthyl)-4-methyl-2-oxo-3-[(trimethylsilyl)oxy]pentyl p-toluenesulfonate
• 英文别名: [(3S)-3-(6-methoxynaphthalen-2-yl)-4-methyl-2-oxo-3-trimethylsilyloxypentyl] 4-methylbenzenesulfonate
• CAS: 727723-03-7
• 化学式: C₂₇H₃₄O₆SSi
• 分子量: 514.715
• InChiKey: BVJABIVKLMVPNK-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  醋酸甲脒 、 (3S)-3-(6-methoxy-2-naphthyl)-4-methyl-2-oxo-3-[(trimethylsilyl)oxy]pentyl p-toluenesulfonate 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 60.0h， 以19.72%的产率得到(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol
  参考文献：
  名称：

  Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

  摘要：

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.035
• 作为产物：
  描述：

  [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](6-methoxy-2-naphthyl)methanone 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 草酰氯 、 氢气 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， -70.0~60.0 ℃ 、101.33 kPa 条件下， 反应 41.83h， 生成 (3S)-3-(6-methoxy-2-naphthyl)-4-methyl-2-oxo-3-[(trimethylsilyl)oxy]pentyl p-toluenesulfonate
  参考文献：
  名称：

  Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

  摘要：

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.035

文献信息

• Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor
  作者：Akio Ojida、Nobuyuki Matsunaga、Tomohiro Kaku、Akihiro Tasaka

  DOI：10.1016/j.tetasy.2004.02.035

  日期：2004.5

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.