90244-32-9

Usage

Uses

Used in Flavoring Industry:
(R)-Methyl 2-hydroxy-3-methylbutanoate is used as a flavoring agent in food and beverages for its pleasant aroma, enhancing the sensory experience of various products.
Used in Perfumery:
(R)-Methyl 2-hydroxy-3-methylbutanoate is used as a fragrance ingredient in perfumes, contributing to the creation of complex and appealing scents.
Used in Cosmetics Production:
(R)-Methyl 2-hydroxy-3-methylbutanoate is used in the production of cosmetics, where its unique properties can be leveraged to improve product performance and sensory attributes.

InChI:InChI=1/C6H12O3/c1-4(2)5(7)6(8)9-3/h4-5,7H,1-3H3/t5-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 640-68-6 D-Val-OH 
• 67-56-1 methanol 
• 3952-67-8 methyl 3-methyl-2-ketobutanoate 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 55109-47-2 3-methyl-2-oxobutanoyl chloride 
• 219598-63-7 8a(S)-3-(2-propyl)-3-hydroxy-4-oxohexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 219598-65-9 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-3-methyl)-butanoyl pyrrolidine 
• 74-88-4 methyl iodide 
• 108-12-3 isopentanoyl chloride 
• 879212-94-9 5,6,7,8-tetrachloro-3-isopropylbenzo[1,4]dioxin-2-one 

Downstream Products

• 90211-81-7 (R)-3-Methyl-2-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid methyl ester 
• 90211-83-9 methyl (R)-2-benzyloxy-3-methylbutanoate 
• 184104-17-4 (R)-2-(4-Methoxy-benzyloxy)-3-methyl-butyric acid methyl ester 
• 381247-05-8 (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester 
• 906535-72-6 C₁₃H₁₈⁽²⁾H₂O₃ 
• 906534-76-7 (3S,4R)-4-Benzyloxymethoxy-3,5-dimethyl-hexanal 
• 906534-75-6 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexan-1-ol 
• 906535-73-7 C₁₆H₂₁⁽²⁾HO₄ 
• 1027964-53-9 (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester 

Relevant academic research and scientific papers

A thermoregulated phase-separable chiral Pt nanocatalyst for recyclable asymmetric hydrogenation of α-ketoesters

The design and preparation of a chiral Pt nanocatalyst system possessing thermoregulated phase-separation property and its application in recyclable asymmetric hydrogenation of α-ketoesters are presented.

Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides

The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues. (Chemical Equation Presented).

Lipodiscamides A-C, new cytotoxic lipopeptides from discodermia kiiensis

Lipodiscamides A-C, three new lipodepsipeptides, were characterized from the marine sponge Discodermia kiiensis. These structurally rare cyclic lipodepsipeptides were found to possess an unprecedented dilactone macrocycle and, thus, represent a new family of lipopeptides. They are the only lipopeptides bearing 4S-hydroxy-trans-2-enoate, and noncanonical amino acids, l-3-ureidoalanine (Uda), E-dehydronorvaline (Denor), and d-citrulline (Cit). MTT assays against P388 and HeLa cells revealed the moderate cytotoxicity of all three compounds.

Lipopeptides from the tropical marine cyanobacterium symploca sp.

A collection of the tropical marine cyanobacterium Symploca sp., collected near Kimbe Bay, Papua New Guinea, previously yielded several new metabolites including kimbeamides A-C, kimbelactone A, and tasihalide C. Investigations into a more polar cytotoxic fraction yielded three new lipopeptides, tasiamides C-E (1-3). The planar structures were deduced by 2D NMR spectroscopy and tandem mass spectrometry, and their absolute configurations were determined by a combination of Marfeys and chiral-phase GC-MS analysis. These new metabolites are similar to several previously isolated compounds, including tasiamide (4), grassystatins (5, 6), and symplocin A, all of which were isolated from similar filamentous marine cyanobacteria.

Lyngbyabellins K-N from two Palmyra atoll collections of the marine cyanobacterium Moorea bouillonii

Five lipopeptides of the lyngbyabellin structure class, four cyclic (1-3 and 5) and one linear (4), were isolated from the extracts of two collections of filamentous marine cyanobacteria obtained from the Palmyra Atoll in the Central Pacific Ocean. Their

Heterocyclic derivatives as modulators of ion channels

The present invention relates to heterocyclic derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives

We report catalytic, enantioselective [4 + 2]-cycloadditions of o-quinones with ketene enolates (derived from readily available acid chlorides) using cinchona alkaloid derivatives as catalysts to produce products in high enantiomeric excess (ee) and good

Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors

The macrolide bafilomycin A1 was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A1 via a conventional carbodiimide-mediated Keck-type macrolactonization.

Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

N-Acylation of prolinol with α-ketoacid chlorides results in concomitant hemiacetalization of the α-keto amide by the prolinol hydroxyl group. (R) or (S) α-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) α-alkyl mandelic acids with good stereoselectivity.

Kinetic Resolution of Chiral α-Hydroperoxy Esters by Horseradish Peroxidase-Catalyzed Enantioselective Reduction to α-Hydroxy Esters

The kinetic resolution of the methyl α-hydroperoxy esters 4 has been investigated by horseradish peroxidase (HRP)-catalyzed reduction to the corresponding optically active α-hydroxy esters 5 in the presence of guaiacol.The method allows for the first time the preparation of enantiomerically pure (ee>97percent) methyl (R)-2-hydroperoxybutyrate (4a).The HRP enzyme is sensitive to the steric demand of the ester alkyl side chain, as manifested by ethyl (ee>97percent) and isopropyl (ee 79percent), while the tert-butyl derivative is not accepted by the enzyme (no reduction).