(2R,3R)-2-amino-3-(4-methoxyphenyl)butyric acid | 132338-27-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3R)-2-amino-3-(4-methoxyphenyl)butyric acid
• 英文别名: (2R,3R)-2-amino-3-(4-methoxyphenyl)butanoic acid
• CAS: 132338-27-3
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: HYOLSKLZTOUWNN-GMSGAONNSA-N

物化性质

• 沸点：
  354.0±37.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-amino-3-(4-methoxyphenyl)butyric acid 在 氢溴酸 作用下， 以90%的产率得到erythro-D-(2R,3R)-β-Methyltyrosine
  参考文献：
  名称：

  异常氨基酸的不对称合成：β-甲基酪氨酸的旋光异构体的合成

  摘要：

  β-甲基酪氨酸的光学纯异构体的合成已经完成。

  DOI：

  10.1016/s0040-4039(01)93367-2
• 作为产物：
  描述：

  (S)-(+)-4'-methoxy-3-phenylbutyric acid 在 palladium on activated charcoal lithium hydroxide 、 双氧水 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 生成 (2R,3R)-2-amino-3-(4-methoxyphenyl)butyric acid
  参考文献：
  名称：

  异常氨基酸的不对称合成：β-甲基酪氨酸的旋光异构体的合成

  摘要：

  β-甲基酪氨酸的光学纯异构体的合成已经完成。

  DOI：

  10.1016/s0040-4039(01)93367-2

文献信息

• A Versatile Chemo-Enzymatic Route to Enantiomerically Pure β-Branched α-Amino Acids
  作者：Geoffrey J. Roff、Richard C. Lloyd、Nicholas J. Turner

  DOI：10.1021/ja049499d

  日期：2004.4.1

  A series of diastereoisomers of beta-methyl-beta-phenylalanine analogues 1a-f have been prepared in enantiomerically pure form using a combination of chemo- and biocatalysis. Starting from l-threonine methyl ester 2, a range of beta,beta-disubstituted didehydroamino acids were obtained as their (Z)-isomers 6a-f. Asymmetric hydrogenation of these alkenes, using either the [Rh(R,R)-Et-DuPhos(COD)]BF4

  一系列β-甲基-β-苯丙氨酸类似物1a-f 的非对映异构体已使用化学和生物催化的组合以对映体纯形式制备。从 l-苏氨酸甲酯 2 开始，获得了一系列 β，β-二取代的双脱氢氨基酸，作为它们的 (Z)-异构体 6a-f。这些烯烃的不对称氢化，使用 [Rh(R,R)-Et-DuPhos(COD)]BF4 或 [Rh(S,S)-Et-DuPhos(COD)]BF4 催化剂，然后水解得到两个β-支链氨基酸的四组可能的非对映异构体。随后的立体反转，使用立体选择性氨基酸氧化酶与非选择性还原剂组合，提供剩余的两组非对映异构体。
• An efficient procedure for the demethylation of aryl-methyl ethers in optically pure unusual amino acids
  作者：Guigm Li、Dinesh Patel、Victor J. Hruby

  DOI：10.1016/s0040-4039(00)73917-7

  日期：1993.1

  An efficient procedure was developed for the removal of methyl groups from aryl methyl ethers, without racemization, in derivatives of unusual amino acids that are of significant importance in the design of highly selective peptide protein ligands with specicific conformational topographical features. Demethylation of aromatic amino acids can result in an appreciable increase in receptor affinity,

  开发了一种有效的方法，用于在不消旋的情况下从芳基甲基醚中去除甲基，而该消旋体是不寻常氨基酸的衍生物，这对设计具有特定构象形貌特征的高选择性肽蛋白质配体具有重要意义。芳香族氨基酸的去甲基化可导致受体亲和力的显着增加，因此，已开发出的新的温和方法代表了Tyr（OMe）衍生物（包括新型侧链环或C-3修饰的类似物）去甲基化的简便实用方法。
• Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine
  作者：Ernesto Nicolas、K. C. Russell、J. Knollenberg、Victor J. Hruby

  DOI：10.1021/jo00078a042

  日期：1993.12

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.