(S)-N^α-tert-butyloxycarbonyl-m-(o-tolyl)tyrosine | 906356-21-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N^α-tert-butyloxycarbonyl-m-(o-tolyl)tyrosine
• 英文别名: (2S)-3-[4-hydroxy-3-(2-methylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 906356-21-6
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: FZBNXMFQTXMWBQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N^α-tert-butyloxycarbonyl-m-(o-tolyl)tyrosine 、 Fmoc-D-缬氨酸 生成 (2R)-2-[[(2S)-2-amino-3-[4-hydroxy-3-(2-methylphenyl)phenyl]propanoyl]amino]-3-methylbutanoic acid
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c
• 作为产物：
  描述：

  Boc-l-3-碘酪氨酸 在 palladium diacetate 、 palladium on activated charcoal 氢气 、 sodium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 乙二醇二甲醚 、 N,N-二甲基乙酰胺 、 水 、 丙酮 为溶剂， 20.0~80.0 ℃ 、100.0 kPa 条件下， 反应 11.0h， 生成 (S)-N^α-tert-butyloxycarbonyl-m-(o-tolyl)tyrosine
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c

文献信息

• Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives
  作者：Sebastian Knör、Burkhardt Laufer、Horst Kessler

  DOI：10.1021/jo060704c

  日期：2006.7.1

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.