114179-07-6

Basic information

• Product Name: (2S,3S)-3-HYDROXY-L-ISOVALINE
• Synonyms: (2S,3S)-3-HYDROXY-L-ISOVALINE;H-SS-IVL(3-OH)-OH;L-Isovaline, 3-hydroxy-, (3S)- (9CI);3-(1,3-dihydroxypropan-2-yloxymethyl)-6-(4-methylphenyl)-5H-imidazo[1,2-a]purin-9-one;3-[(2-hydroxy-1-methylol-ethoxy)methyl]-6-(4-methylphenyl)-5H-imidazo[1,2-a]purin-9-one
• CAS NO: 114179-07-6
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.15
• Product Categories: GLYCINESCAFFOLD
• Mol File: 114179-07-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3S)-3-HYDROXY-L-ISOVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-HYDROXY-L-ISOVALINE(114179-07-6)
• EPA Substance Registry System: (2S,3S)-3-HYDROXY-L-ISOVALINE(114179-07-6)

Safety Data

• Hazardous Substances Data: 114179-07-6(Hazardous Substances Data)

Usage

General Description

(2S,3S)-3-Hydroxy-L-isovaline is a chemical compound that belongs to the category of isovaline derivatives. It is a stereochemically defined amino acid that contains a hydroxyl group attached to the third carbon and an isovaline side chain. (2S,3S)-3-HYDROXY-L-ISOVALINE has been shown to exhibit antimicrobial properties, making it potentially useful in the development of new antimicrobial agents. Additionally, (2S,3S)-3-Hydroxy-L-isovaline has also been studied for its potential as a building block in the synthesis of peptidomimetic molecules, which are compounds designed to mimic the structure and function of peptides. Overall, this chemical compound has demonstrated potential applications in medicine and drug development.

Upstream product

• 1213233-69-2 isopropyl (S,S)-2-benzoylamino-3-hydroxy-2-methylbutyrate 
• 152036-29-8 (2S,5S)-5-Acetyl-3,5-dimethyl-4-oxoimidazolidin-1-carbonsaeure-t-butylester 
• 211805-80-0 (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester 
• 211805-84-4 (2S,3S)-2-Bromo-3-hydroxy-2-methyl-butyric acid benzyl ester 
• 211805-79-7 benzyl (2R,3S)-2,3-dihydroxy-2-methylbutanoate 
• 37526-88-8 benzyl tiglate 
• 677344-59-1 (1S,7aR)-1,5,5,7a-tetramethyl-2,6-dioxa-4-azapentalen-3-one 
• 677344-58-0 (4R,1'S)-N-(tert-butoxycarbonyl)-4-(1'-hydroxyethyl)-2,2,4-trimethyloxazolidine 
• 211805-81-1 (2S,3S)-2-Azido-3-hydroxy-2-methyl-butyric acid benzyl ester 
• 152036-30-1 (2S,5S,1'S)-5-(1'-Hydroxyethyl)-3,5-dimethyl-4-oxoimidazolidin-1-carbonsaeure-t-butylester 
• 88318-69-8 (4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester 

Relevant articles and documents

α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: Application in the synthesis of all stereoisomers of α- methylthreonine

The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different β-substituted α-methylserines.

Novel Enantioselective Synthesis of α-Methylthreonines and α,β-Dimethylcysteines

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Preparation of (R,R)- or (S,S)-2-Amino-3-hydroxycarboxylic Acids (allo-Threonine Analogs) by Acylation/Reduction of t-Butyl 2-t-Butyl-3-methyl-4-oxoimidazolidine-1-carboxylate (Boc-BMI)

While there are numerous methods of preparing threonine analogs by aldol additions of chiral glycine derivatives to aldehydes, only few general routes leading to the epimers with C,C-bond formation are presently available.This paper describes the acylation of the title compound 1 with acyl chlorides (-> trans-products 2-9), the subsequent reduction with LiBHEt3 in THF (-> hydroxyalkylated BMI derivatives 10-14), and acidic hydrolysis to the free allo-threonines 18-22.The first two steps are totally stereoselective (by NMR analysis), and the overall yields from BocBMI are in the order of 30-60percent.Only allo-threonines without branching in the γ-position are accessible by this method.In one case we have also applied this sequence of steps to prepare an α-branched allo-threonine derivative 26. - The 5-acyl-BocBMI derivatives 2-9 are remarkably stable to epimerization at the center between the two carbonyl groups.Possible reasons for this are discussed and are partially supported by an X-ray crystal structure analysis of the phenacetyl derivative 6. Key words: EPC synthesis of amino acids; non-proteinogenic amino acids; diastereoselective reduction with superhydride (LiBHEt3)