(S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester | 220024-53-3

• 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: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-(4-bromophenyl)-2-[[(1R)-2-hydroxy-1-phenylethyl]-phenylmethoxycarbonylamino]propanoate
• CAS: 220024-53-3
• 化学式: C₂₆H₂₆BrNO₅
• 分子量: 512.4
• InChiKey: FWHYRIQMSUWGLL-OZXSUGGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester 在 lead(IV) acetate 、 盐酸 、 甲醇 、 palladium diacetate 、 sodium hydroxide 、 1,3-双(二苯基膦)丙烷 、 三乙胺 、 methyloxirane 作用下， 以 二甲基亚砜 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 (S)-alpha-甲基-4-羧基苯甘氨酸
  参考文献：
  名称：

  Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors

  摘要：

  Heating a mixture of alpha-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated alpha-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-alpha M4CPG, (S)-MPPG, (S)AIDA, and (S)-APICA, are synthesized.

  DOI：

  10.1021/jo981297a
• 作为产物：
  描述：

  氯甲酸苄酯 、 N-[(R)-(2-hydroxy-1-phenylethyl)]-(S/R)-2-amino-2-methyl-(4'-bromophenyl)acetic acid methyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以23%的产率得到(R)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors

  摘要：

  Heating a mixture of alpha-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated alpha-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-alpha M4CPG, (S)-MPPG, (S)AIDA, and (S)-APICA, are synthesized.

  DOI：

  10.1021/jo981297a

文献信息

• Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (<i>S</i>)-αM4CPG, (<i>S</i>)-MPPG, (<i>S</i>)-AIDA, and (<i>S</i>)-APICA, the Antagonists of Metabotropic Glutamate Receptors
  作者：Dawei Ma、Hongqi Tian、Guixiang Zou

  DOI：10.1021/jo981297a

  日期：1999.1.1

  Heating a mixture of alpha-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated alpha-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-alpha M4CPG, (S)-MPPG, (S)AIDA, and (S)-APICA, are synthesized.