N^α-acetyl-1-(4-tert-butyldimethylsilyloxy)naphthylalanine methyl ester | 906356-28-3

• 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: N^α-acetyl-1-(4-tert-butyldimethylsilyloxy)naphthylalanine methyl ester
• 英文别名: Methyl 2-acetamido-3-[4-[tert-butyl(dimethyl)silyl]oxynaphthalen-1-yl]propanoate
• CAS: 906356-28-3
• 化学式: C₂₂H₃₁NO₄Si
• 分子量: 401.578
• InChiKey: MWFQLVNMERYXHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N^α-acetyl-1-(4-tert-butyldimethylsilyloxy)naphthylalanine methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 2-Acetylamino-3-(4-hydroxy-naphthalen-1-yl)-propionic acid methyl ester
  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：

  methyl 2-(benzyloxycarbonyl)amino-3-(1-(tert-butyldimethylsilyloxy)naphthalen-4-yl)acrylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 20.0h， 生成 N^α-acetyl-1-(4-tert-butyldimethylsilyloxy)naphthylalanine methyl ester
  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