(2S,3S)-3-amino-2-methyl butyric acid | 139344-68-6

• 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: (2S,3S)-3-amino-2-methyl butyric acid
• 英文别名: (2S,3S)-3-amino-2-methyl-butyric acid；2(S)-methyl-3(S)-aminobutanoic acid；(3S)-L-Valinic acid；(2S,3S)-3-amino-2-methylbutanoic acid
• CAS: 139344-68-6
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: RRWPLOJQTOADRZ-IMJSIDKUSA-N

物化性质

• 沸点：
  220.7±23.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-amino-2-methyl butyric acid 在 N-甲基吗啉 、 ammonium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[(2S,3S)-4-amino-3-methyl-4-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model

  摘要：

  An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.102
• 作为产物：
  描述：

  (2S,3S)-2-cyano-3-[N-(4-nitrobenzoyl)amino]butane 在 双氧水 、 sodium carbonate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 65.0h， 生成 (2S,3S)-3-amino-2-methyl butyric acid
  参考文献：
  名称：

  Catalytic Enantioselective Desymmetrization of meso-N-Acylaziridines with TMSCN

  摘要：

  A catalytic enantioselective desymmetrization of meso-N-p-nitrobenzoylaziridines with TMSCN was developed using a chiral gadolinium catalyst generated from Gd(OiPr)3 and d-glucose-derived ligand 1. In this reaction, the addition of a catalytic amount of trifluoroacetic acid (TFA) improved enantioselectivity. High enantioselectivity was obtained from a range of meso-aziridines at 0-60 degrees C. The product could be easily transformed into beta-amino acids. Thus, the developed catalytic enantioselective desymmetrization reaction allowed for efficient catalytic synthesis of chiral cyclic beta-amino acids. The incorporation of TFA into the catalyst complex was observed using ESI-MS. Generation of this new complex might be the origin of the improved enantioselectivity.

  DOI：

  10.1021/ja053486y

文献信息

• Diastereoselective synthesis of β-amino acid derivatives from dihydropyridones
  作者：Markus Ege、Klaus T. Wanner

  DOI：10.1016/j.tet.2008.05.073

  日期：2008.7

  A new method for the diastereoselective preparation of stereoisomeric 2,3-disubstituted β-amino acids is presented. It is based on trans- and cis-2,3-disubstituted dihydropyridones, which were derived from 2-monosubstituted N-acyl dihydropyridone derivatives. Alkylation of the enolates of 2-substituted dihydropyridones gave trans-2,3-disubstituted dihydropyridones with high diastereoselectivities.

  提出了一种非对映选择性制备立体异构体2,3-二取代的β-氨基酸的新方法。它是基于反式-和顺-2,3-二取代的二氢吡啶，将其衍生自2单取代Ñ酰基二氢吡啶酮衍生物。2-取代的二氢吡啶酮的烯醇盐的烷基化得到具有高非对映选择性的反式-2,3-二取代的二氢吡啶酮。通过去质子化/再质子化序列使二氢吡啶酮核的C-3处的立体中心反转，从而以高收率和非对映选择性产生了立体异构体顺式-2,3-二取代的二氢吡啶酮。除去N之后-酰基保护基团，高碘酸钠分别氧化生成的顺式或反式-2,3-异位二氢吡啶酮，导致相应的非对映体β-氨基酸氧化降解。
• Toward a rational design of the assembly structure of polymetallic asymmetric catalysts: design, synthesis, and evaluation of new chiral ligands for catalytic asymmetric cyanation reactions
  作者：Ikuo Fujimori、Tsuyoshi Mita、Keisuke Maki、Motoo Shiro、Akihiro Sato、Sanae Furusho、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2007.02.081

  日期：2007.6

  New chiral ligands (4 and 5) for polymetallic asymmetric catalysts were designed based on the hypothesis that the assembled structure should be stable when made from a stable module 8. A metal-ligand 5:6+mu-oxo+OH complex was generated from Gd((OPr)-Pr-i)(3) and 4 or 5, and this complex was an improved asymmetric catalyst for the desymmetrization of meso-aziridines with TMSCN and conjugate addition of TMSCN to alpha,beta-unsaturated N-acylpyrroles, compared to the previously reported catalysts derived from 1-3. These two groups of catalysts produced opposing enantioselectivity even though the ligands had the same chirality. The functional difference in the asymmetric catalysts is derived from differences in the higher-order structure of the polymetallic catalysts. (C) 2007 Elsevier Ltd. All rights reserved.
• α-Alkylation of β-aminobutanoates with lk-1.2-induction
  作者：Dieter Seebach、Heinrich Estermann

  DOI：10.1016/s0040-4039(00)96296-8

  日期：1987.1
• Enzymatic Resolution of α-Alkyl β-Amino Acids Using Immobilized Penicillin G Acylase
  作者：Giuliana Cardillo、Alessandra Tolomelli、Claudia Tomasini

  DOI：10.1021/jo9613500

  日期：1996.1.1
• Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid
  作者：Eusebio Juaristi、Jaime Escalante

  DOI：10.1021/jo00060a051

  日期：1993.4

  The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle was alkylated (LDA, methyl iodide, or benzyl bromide) to afford the like and unlike diastereomeric products in a 80:20 ratio. Separation and hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free, enantiomerically pure, amino acids 11-14.