26287-62-7

Basic information

• Product Name: H-ALPHA-ME-DL-VAL-OH
• Synonyms: H-α-Me-DL-Val-OH;α-Methyl-DL-valine;α-Me-DL-Val-OH;α-Methyl-DL-valine≥ 99% (assay);ALPHA-ME-DL-VALINE;ALPHA-METHYL-DL-VALINE;H-ALPHA-ME-DL-VAL-OH;H-DL-(ME)VAL-OH
• CAS NO: 26287-62-7
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• Product Categories: GLYCINESCAFFOLD
• Mol File: 26287-62-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 293 °C (sublm)
• Boiling Point: 217.7 °C at 760 mmHg
• Flash Point: 85.5 °C
• Appearance: /
• Density: 1.038 g/cm³
• Vapor Pressure: 0.0499mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: Store at RT.
• PKA: 2.40±0.14(Predicted)
• CAS DataBase Reference: H-ALPHA-ME-DL-VAL-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-ALPHA-ME-DL-VAL-OH(26287-62-7)
• EPA Substance Registry System: H-ALPHA-ME-DL-VAL-OH(26287-62-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 26287-62-7(Hazardous Substances Data)

Usage

Chemical Properties

Almost white powder

InChI:InChI=1/C6H13NO2/c1-4(2)6(3,7)5(8)9/h4H,7H2,1-3H3,(H,8,9)

Upstream product

• 98262-58-9 (2R,5S)-1-benzoyl-2-(tert-butyl)-5-isopropyl-3,5-dimethylimidazolidin-4-one 
• 1025364-74-2 (S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one 
• 97443-93-1 (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on 
• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 53940-86-6 DL-N-Trifluoroacetyl-α-methylvalin 
• 1007599-18-9 (S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one 
• 137584-40-8 (S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid 

Downstream Products

• 169566-81-8 (S)-N²-<(9H-fluoren-9-yl)methoxycarbonyl>-2-methylvaline 
• 1234494-16-6 C₉H₁₃N₂O₂^(1-)*Na⁽¹⁺⁾ 
• 711015-20-2 Cbz-D-Pro-L-(αMe)Val-L-Phe-OMe 
• 711015-19-9 Cbz-L-(αMe)Val-L-Phe-OMe 
• 409320-07-6 Cbz-L-(α-Me)Val-NH-t-Bu 
• 137584-40-8 (S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid 
• 551964-00-2 4-isopropyl-2-(3-methoxy-2-methyl-phenyl)-4-methyl-4H-oxazol-5-one 
• 467221-69-8 (S)-2-Azido-2,3-dimethyl-butyric acid 
• 53940-90-2 (S)-2-((tert-butoxycarbonyl)amino)-2,3-dimethylbutanoic acid 
• 135610-84-3 2-(2-chloro-acetylamino)-2,3-dimethyl-butyric acid 
• 301222-28-6 (S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-hydroxymethyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester 
• 301222-29-7 (S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-formyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester 
• 679400-64-7 2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-hydroxymethyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 
• 956102-64-0 methylvalinol 

Relevant articles and documents

Memory of chirality of tertiary aromatic amides: A simple and efficient method for the enantioselective synthesis of quaternary α-amino acids

A new methodology for the asymmetric synthesis of quaternary R-substituted amino acids using memory of chirality has been developed. The strategy utilizes the dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during an enolization step. Starting from five different L-amino acids, the corresponding oxazolidin-5-ones containing a tertiary aromatic amide group have been synthesized in one step and then alkylated with various electrophiles, with good yields and enantioselectivities (up to 96% and up to >99% after recrystallization). One-step deprotection affords enantioenriched or enantiopure quaternary α-amino acids. We describe here the optimization process, the results obtained in each series and a plausible explanation, based on NMR studies, DFT calculations and crystallographic structures. The methodology presented herein constitutes an efficient synthesis of enantiopure quaternary R-amino acids (three steps only) starting from tertiary L-amino acids, without any external source of chirality.

Enantioselective synthesis and enantiomeric amplification of amino acids under prebiotic conditions

(Chemical Equation Presented) A plausible origin of biomolecular homochirality is advanced, where α-methyl amino acids found on meteorites transfer their chirality in the synthesis of normal amino acids. This asymmetry can be amplified to nearly homochiral levels, thus providing the necessary prerequisite for life to start on this planet and elsewhere in the universe.

Chiral 2-cyano esters as synthetic intermediates in the synthesis of R and S-α-methylvaline

A divergent stereoselective synthesis of R and S α-methylvaline from (2RS) (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-3-methylbutanoate has been developed.