127126-06-1

Basic information

• Product Name: (2S,3R)-3-HYDROXY-L-ISOVALINE
• Synonyms: H-SR-IVL(3-OH)-OH;(2S,3R)-3-HYDROXY-L-ISOVALINE;L-Isovaline, 3-hydroxy-, (3R)- (9CI)
• CAS NO: 127126-06-1
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.15
• Product Categories: GLYCINESCAFFOLD
• Mol File: 127126-06-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 317.3±32.0 °C(Predicted)
• Appearance: /
• Density: 1.240±0.06 g/cm3(Predicted)
• PKA: 2.23±0.14(Predicted)
• CAS DataBase Reference: (2S,3R)-3-HYDROXY-L-ISOVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-HYDROXY-L-ISOVALINE(127126-06-1)
• EPA Substance Registry System: (2S,3R)-3-HYDROXY-L-ISOVALINE(127126-06-1)

Safety Data

• Hazardous Substances Data: 127126-06-1(Hazardous Substances Data)

Usage

General Description

"(2S,3R)-3-HYDROXY-L-ISOVALINE" is a chemical compound that belongs to the class of amino acids. It is a derivative of isovaline and has a 3-hydroxy group attached to its structure. (2S,3R)-3-HYDROXY-L-ISOVALINE has a specific stereochemistry, with the 2S and 3R configuration. It is a rare amino acid that has been identified in certain natural products and has potential pharmacological and bioactive properties. Its unique structure and properties make it a subject of interest in various fields of research, including medicinal chemistry and drug development.

Upstream product

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• 1213233-82-9 (4S,5R)-4-isopropoxycarbonyl-4,5-dimethyl-2-phenyl-1,3-oxazoline 
• 211805-87-7 (2S,3R)-2-Azido-3-hydroxy-2-methyl-butyric acid isobutyl ester 
• 211805-85-5 isobutyl (2R,3R)-2,3-dihydroxy-2-methylbutanoate 
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• 677344-61-5 (1R,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 
• 211805-88-8 (2S,3R)-2-Amino-3-hydroxy-2-methyl-butyric acid isobutyl ester 
• 211805-86-6 (4R,5R)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid isobutyl ester 

Relevant articles and documents

α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-l-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of α-methylthreonine by an α-alkylation reaction and in the synthesis of chiral α,β-dehydroamino acid derivatives, using the tandem retro-O-Michael/γ-alkylation reactions as key steps.

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.

Efficient syntheses of the four enantiomers and diastereomers of α-methylthreonine and both enantiomers of α-methylserine

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