127060-92-8

Basic information

• Product Name: (2R,3S)-3-HYDROXY-D-ISOVALINE
• Synonyms: H-RS-IVL(3-OH)-OH;(2R,3S)-3-HYDROXY-D-ISOVALINE;D-Isovaline, 3-hydroxy-, (3S)- (9CI)
• CAS NO: 127060-92-8
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.15
• Product Categories: GLYCINESCAFFOLD
• Mol File: 127060-92-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,3S)-3-HYDROXY-D-ISOVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-HYDROXY-D-ISOVALINE(127060-92-8)
• EPA Substance Registry System: (2R,3S)-3-HYDROXY-D-ISOVALINE(127060-92-8)

Safety Data

• Hazardous Substances Data: 127060-92-8(Hazardous Substances Data)

Usage

General Description

(2R,3S)-3-HYDROXY-D-ISOVALINE is a chiral amino acid derivative that is a synthetic analog of L-isovaline, a non-proteinogenic amino acid found in meteorites. It has a molecular formula of C5H11NO3 and a molecular weight of 133.15 g/mol. (2R,3S)-3-HYDROXY-D-ISOVALINE plays a role in the study of prebiotic chemistry and the origins of life, as it is related to the formation of amino acids in extraterrestrial environments. It has also been investigated for its potential as a building block for the synthesis of peptide libraries and as an intermediate in the preparation of other bioactive compounds. Additionally, (2R,3S)-3-HYDROXY-D-ISOVALINE has been studied for its pharmacological properties and potential therapeutic applications.

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Relevant articles and documents

Asymmetric synthesis of all stereoisomers of a-methylthreonine using an organocatalytic steglich rearrangement reaction as a key step

An efficient synthetic route to all four stereoisomers of a-methylthreonine has been established. Each type of stereoisomer has been isolated in diastereomerically pure form and with an enantiomeric excess of at least 86% ee. The key step in this multi-st

Functionalised 2,3-dimethyl-3-aminotetrahydrofuran-4-one and N-(3-oxo-hexahydrocyclopenta[b]furan-3a-yl)acylamide based scaffolds: Synthesis and cysteinyl proteinase inhibition

A stereoselective synthesis of functionalised (2R,3R)-2,3-dimethyl-3- amidotetrahydrofuran-4-one, its (2S,3R)-epimer and (3aR,6aR)-N-(3-oxo- hexahydrocyclopenta[b]furan-3a-yl)acylamide cysteinyl proteinase inhibitors has been developed using Fmoc-protected scaffolds 6-8 in a solid-phase combinatorial strategy. Within these scaffolds, the introduction of an alkyl substituent α to the ketone affords chiral stability to an otherwise configurationally labile molecule. Preparation of scaffolds 6-8 required stereoselective syntheses of suitably protected α-diazomethylketone intermediates 9-11, derived from appropriately protected α-methylthreonines (2R,3R)-12, (2R,3S)-13 and a protected analogue of (1R,2R)-1-amino-2- hydroxycyclopentanecarboxylic acid 14. Application of standard methods for the preparation of amino acid α-diazomethylketones, through treatment of the mixed anhydride or pre-formed acyl fluorides of intermediates 12-14 with diazomethane, proved troublesome giving complex mixtures. However, the desired α-diazomethylketones were isolated and following a lithium chloride/acetic acid promoted insertion reaction provided scaffolds 6-8. Elaboration of 6-8 on the solid phase gave α,β-dimethyl monocyclic ketone based inhibitors 38a-f, 39a,b,d,e,f and bicyclic inhibitors 40a-e that exhibited low micromolar activity against a variety of cysteinyl proteinases.