4-[(tert-butoxycarbonyl)amino]-2-methylbutanoic acid | 79799-26-1

• 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: 4-[(tert-butoxycarbonyl)amino]-2-methylbutanoic acid
• 英文别名: rac-4-([(tert-butoxy)carbonyl]amino)-2-methylbutanoic acid；Boc-γ2-HHAla-OH；(2R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 79799-26-1
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: NMXJIDPAYKUADJ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(tert-butoxycarbonyl)amino]-2-methylbutanoic acid 在 N-甲基吗啉 、 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 双氧水 、 三甲基铝 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 45.0h， 生成 2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Total synthesis of (+)-calyculin A

  摘要：

  A convergent asymmetric synthesis of the marine natural product calyculin A has been accomplished through the union of the two subunits comprising the C1-C25 and C26-C37 portions of the molecule. These fragments were constructed utilizing auxiliary-based asymmetric aldol, alkylation, hydroxylation, and Michael reactions to establish 10 of the 15 stereogenic centers, The remaining chirality was incorporated through internal asymmetric induction. Stereoselective Wittig coupling of the two fragments and subsequent deprotection provided synthetic calyculin A. The spectral properties of the synthetic material were in complete agreement with those of the natural material except for the optical rotation which was equal and opposite in sign to that of the natural material. The absolute configuration of (-)-calyculin A has thus been shown to be opposite to that illustrated in structure 1.

  DOI：

  10.1021/ja00050a024
• 作为产物：
  描述：

  (S)-4-isopropyl-3-[(R)-2-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one 在 镍 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 21.0h， 生成 4-[(tert-butoxycarbonyl)amino]-2-methylbutanoic acid
  参考文献：
  名称：

  Enantioselective Preparation of γ ‐Amino Acids and γ ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2365::aid-hlca2365>3.0.co;2-#

文献信息

• [EN] INHIBITING TRABID<br/>[FR] INHIBITION DE TRABID
  申请人：INTEGRAL EARLY DISCOVERY INC

  公开号：WO2020227168A1

  公开（公告）日：2020-11-12

  The present disclosure is directed to compounds of formulas (I) - (VII), which are useful as modulators of TRABID. The compounds are further useful in the inhibition of TRABID and the treatment of diseases or disorders associated with the inhibition of TRABID. For instance, the disclosure is concerned with compounds and compositions for inhibition of TRABID, methods of treating diseases associated with the inhibition of TRABID (e.g., autoimmune inflammatory diseases including, but not limited to, psoriasis), and methods of synthesis of these compounds.

  本公开涉及化合物的结构式(I) - (VII)，这些化合物可作为TRABID的调节剂。这些化合物进一步可用于抑制TRABID并治疗与TRABID抑制相关的疾病或紊乱。例如，本公开涉及用于抑制TRABID的化合物和组合物，治疗与TRABID抑制相关的疾病的方法（例如，包括但不限于自身免疫性炎症性疾病，如牛皮癣），以及这些化合物的合成方法。
• Effect of the Substituent and Amino Group Position on the Lipase‐Catalyzed Resolution of γ‐Amino Esters: A Molecular Docking Study Shedding Light on<i>Candida antarctica</i>lipase B Enantioselectivity
  作者：Marina A. Ortega‐Rojas、Edmundo Castillo、Rodrigo Said Razo‐Hernández、Nina Pastor、Eusebio Juaristi、Jaime Escalante

  DOI：10.1002/ejoc.202100712

  日期：2021.9.14

  In contrast to N-protected β3-amino esters, the Candida antarctica lipase B catalyzed kinetic resolution of amino esters holding alpha (γ2), beta (γ3), and gamma (γ4) stereocenters is strongly compromised by steric factors at the level of the catalytic cavity. Molecular docking studies helped establish that the steric exclusion region involves the Ile189 and Val190 residues and the amino bonding region

  与N保护的 β 3氨基酯相比，南极念珠菌脂肪酶 B 催化的氨基酯的动力学拆分具有 α ( γ 2 )、β ( γ 3 ) 和 γ ( γ 4 ) 立体中心，在催化腔的高度。分子对接研究有助于确定空间排斥区域涉及 Ile189 和 Val190 残基以及氨基键合区域，其中有利于与 Asp134 残基的氢键。
• [EN] CONJUGATES AND METHODS OF USING THE SAME<br/>[FR] CONJUGUÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：FLAGSHIP PIONEERING INNOVATIONS V INC

  公开号：WO2020037009A8

  公开（公告）日：2020-03-26
• Determination of Enantiomer Purity ofβ- andγ-Amino Acids by NMR Analysis of Diastereoisomeric Palladium Complexes
  作者：Andreas Böhm、Dieter Seebach

  DOI：10.1002/1522-2675(20001220)83:12<3262::aid-hlca3262>3.0.co;2-p

  日期：2000.12.20

  Like alpha -amino acids, beta- and gamma -amino acids form spirobicyclic complexes (see 2 and 3) by reaction with the chiral di-mu -chlorobis2-[1-dimethylamino-xN)-ethyl]phenyl-xC}dipalladium complexes 1 under basic conditions (Scheme 1 and X-ray structures in Fig. I). The diastereoisomeric complexes formed with mixtures of enantiomers of either the amino acids or the dichloro-dipalladium complexes give rise to marked chemical-shift differences in the H-1- and C-13-NMR spectra (Figs. 2-4) to allow determination of the enantiomer purities. A simple procedure is described by which beta- and gamma -amino acids (which may be generated in situ from Boc- or Fmoc-protected precursors) are converted to the Pd complexes and subjected to NMR measurements. The effects of solvent, temperature, and variation of the aryl group in the chiral derivatizing Pd reagent are described (Figs. 4 and 5). The methyl esters of B-amino acids can also be employed, forming diastereoisomeric chloro[(amino-xN)aryl-xC][(amino-xN)alkanoate]palladium complexes 6 for determining enantiomer ratios (Scheme 6). The new method has great scope, as demonstrated for beta (2)-, beta (3), beta (2,3)-, beta (2,2,3)-, gamma (2)-, gamma (3)-, gamma (4)-, and gamma (2,3,4)- amino acid derivatives.
• Asymmetric synthesis of calyculin A. 2. The C26-C37 .gamma.-amino acid fragments
  作者：David A. Evans、James R. Gage、James L. Leighton、Annette S. Kim

  DOI：10.1021/jo00033a010

  日期：1992.3

  New chiral imide enolate alkylation, aldol, and Michael addition bond constructions have been employed in the asymmetric synthesis of the C26-C37 portion of calyculin A.