(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4-diethylphosphono)benzyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one | 690254-41-2

• 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: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4-diethylphosphono)benzyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: benzyl (3S,5S,6R)-3-[(4-diethoxyphosphorylphenyl)methyl]-3-methyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 690254-41-2
• 化学式: C₃₆H₃₈NO₇P
• 分子量: 627.674
• InChiKey: WDMSGCBUZYRONT-PDRDTOBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4-diethylphosphono)benzyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 在 palladium on activated charcoal 氢气 、 苯甲醚 、 三乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 122.17h， 生成 N-{(S)-1-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-2-[4-(diethoxy-phosphoryl)-phenyl]-1-methyl-ethyl}-oxalamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

  摘要：

  Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.005
• 作为产物：
  描述：

  4-碘苄基溴 在 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.58h， 生成 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4-diethylphosphono)benzyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

  摘要：

  Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.005

文献信息

• Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics
  作者：Shinya Oishi、Sang-Uk Kang、Hongpeng Liu、Manchao Zhang、Dajun Yang、Jeffrey R. Deschamps、Terrence R. Burke

  DOI：10.1016/j.tet.2004.02.005

  日期：2004.3

  Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved.