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Cas Database

53940-83-3

53940-83-3

Identification

Synonyms:L-Isovaline,3-methyl- (9CI); (S)-2-Methylvaline; (S)-a-Methylvaline; L-a-Methylvaline

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Safety information and MSDS

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  • Manufacture/Brand:Usbiological
  • Product Description:a-Methyl-L-valine
  • Packaging:500mg
  • Price:$ 368
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:α-Methyl-L-valine
  • Packaging:500mg
  • Price:$ 95
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  • Manufacture/Brand:TRC
  • Product Description:α-Methyl-L-valine
  • Packaging:5g
  • Price:$ 665
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(S)-(?)-α-Methylvaline 99%, ≥98.5% (TLC)
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:α-Methyl-L-valine
  • Packaging:2.5 g
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:α-Methyl-L-valine
  • Packaging:12.5 g
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  • Manufacture/Brand:Iris Biotech GmbH
  • Product Description:H-alpha-Me-L-Val-OH
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  • Manufacture/Brand:Iris Biotech GmbH
  • Product Description:H-alpha-Me-L-Val-OH
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  • Manufacture/Brand:Crysdot
  • Product Description:(S)-2-Amino-2,3-dimethylbutanoicacid 95+%
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  • Manufacture/Brand:Crysdot
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Relevant articles and documentsAll total 12 Articles be found

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

Branca, Mathieu,Pena, Sebastien,Guillot, Regis,Gori, Didier,Alezra, Valerie,Kouklovsky, Cyrille

scheme or table, p. 10711 - 10718 (2009/12/04)

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

Levine, Mindy,Kenesky, Craig Scott,Mazori, Daniel,Breslow, Ronald

supporting information; experimental part, p. 2433 - 2436 (2009/05/27)

(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

Cativiela,Diez-De-Villegas,Galvez,Lapena

, p. 5921 - 5928 (2007/10/02)

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

Process route upstream and downstream products

Process route

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one
1007599-18-9

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one

Conditions
Conditions Yield
With hydrogen bromide; In 1,4-dioxane; for 3h; Heating;
100%
(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one
1025364-74-2

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one

Conditions
Conditions Yield
(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one; With hydrogen bromide; In water; Reflux; Inert atmosphere;
With Dowex-H+; Inert atmosphere;
100%
(S)-methyl 2-benzamido-2,3-dimethylbutanoate

(S)-methyl 2-benzamido-2,3-dimethylbutanoate

Conditions
Conditions Yield
With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 12h;
87.4%
(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid
137584-40-8

(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid

Conditions
Conditions Yield
With 10% Pd on charcoal; cyclohexene; In ethanol; for 1h; Reflux;
83%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

(+)-(R)-2-amino-2,3-dimethylbutanamide
90376-98-0

(+)-(R)-2-amino-2,3-dimethylbutanamide

Conditions
Conditions Yield
In water; at 37 ℃; Ochrobactrum anthropi NCIMB 40321;
74%
86%
With water; at 37 ℃; for 72h; aminopeptidase from Mycobacterium neoaurum ATCC 25795;
(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on
97443-93-1

(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C
2: tetrahydrofuran; hexane / 2 h / -78 - 0 °C
3: 1.) 6 N HCl, 2.) Dowex 50 WX / 1.) water, 175 deg C to 185 deg C, 4 h; 2.) water
With hydrogenchloride; Dowex 50 WX; lithium diisopropyl amide; In tetrahydrofuran; hexane;
Lithium; (R)-1-benzoyl-2-tert-butyl-5-isopropyl-3-methyl-2,3-dihydro-1H-imidazol-4-olate

Lithium; (R)-1-benzoyl-2-tert-butyl-5-isopropyl-3-methyl-2,3-dihydro-1H-imidazol-4-olate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrahydrofuran; hexane / 2 h / -78 - 0 °C
2: 1.) 6 N HCl, 2.) Dowex 50 WX / 1.) water, 175 deg C to 185 deg C, 4 h; 2.) water
With hydrogenchloride; Dowex 50 WX; In tetrahydrofuran; hexane;
DL-N-Trifluoroacetyl-α-methylvalin
53940-86-6

DL-N-Trifluoroacetyl-α-methylvalin

Conditions
Conditions Yield
With sodium hydroxide; (enzymatic transformation);
(SS)-{Ni(O<sub>2</sub>CC(CH(CH<sub>3</sub>)2)(CH<sub>3</sub>)NCHC<sub>6</sub>H<sub>4</sub>NCOC<sub>4</sub>H<sub>7</sub>N(CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>))}*1.5H<sub>2</sub>O

(SS)-{Ni(O2CC(CH(CH3)2)(CH3)NCHC6H4NCOC4H7N(CH2C6H5))}*1.5H2O

Conditions
Conditions Yield
75%
(2S) methyl 2-methoxycarbonylamino-2,3-dimethylbutanoate

(2S) methyl 2-methoxycarbonylamino-2,3-dimethylbutanoate

Conditions
Conditions Yield
With hydrogenchloride; methyloxirane; Yield given. Multistep reaction; 1.) reflux, 12 h, 2.) EtOH, reflux, 30 min;

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