(1'S,2'R)-(-)-N-<2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide | 158705-93-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1'S,2'R)-(-)-N-<2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide
• 英文别名: N-[(1S,2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-(3,4-dimethoxyphenyl)-1-phenylethyl]acetamide
• CAS: 158705-93-2
• 化学式: C₃₄H₃₉NO₄Si
• 分子量: 553.773
• InChiKey: PTDSFPAVBXVZOB-JHOUSYSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'S,2'R)-(-)-N-<2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide 在 sodium tetrahydroborate 、 五氯化磷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (1R,3S,4R)-(+)-6,7-dimethoxy-4-hydroxy-1-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines

  摘要：

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.

  DOI：

  10.1016/0957-4166(94)80127-4
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)-2-hydroxyacetonitrile 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1'S,2'R)-(-)-N-<2-(tert-butyldiphenylsilyloxy)-2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide
  参考文献：
  名称：

  A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines

  摘要：

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.

  DOI：

  10.1016/0957-4166(94)80127-4

文献信息

• A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines
  作者：Imanol Tellitu、Dolores Badía、Esther Domíguez、Francisco J. García

  DOI：10.1016/0957-4166(94)80127-4

  日期：1994.8

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.