84567-98-6

Usage

Uses

Used in Medical Research:
3-Hydroxy-2-methyl-(2S,3S)-Butanoic acid is utilized as an analyte in the study of patients with β-ketothiolase deficiency. This condition is a rare genetic disorder that affects the body's ability to process certain amino acids and is characterized by the accumulation of toxic substances in the blood and urine. 3-hydroxy-2-methyl-(2S,3S)-Butanoic acid serves as a biomarker for diagnosing and monitoring the progress of the disease.
Used in Pharmaceutical Synthesis:
3-Hydroxy-2-methyl-(2S,3S)-Butanoic acid is employed in the synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium, an infectious bacterium. This bacterium is responsible for causing infections in humans and animals, particularly in individuals with weakened immune systems. 3-hydroxy-2-methyl-(2S,3S)-Butanoic acid plays a crucial role in the development of diagnostic tools and potential therapeutic agents targeting this pathogen.

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 75-07-0 acetaldehyde 
• 535-11-5 Ethyl 2-bromopropionate 
• 684-84-4 2-methyl-1,3-butanediol 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 
• 870785-29-8 14β-O-(2S,3S-nilyl)-2α,3β,5β,6β,16α-pentahydroxygrayanane 
• 1253963-44-8 C₆₈H₁₁₈O₃₅ 
• 1253963-45-9 methyl 3S,11S-dihydroxytetradecanoate 11-O-α-L-rhamnopyranosyl-(1->3)-O-[4-O-2R-methyl-3R-O-(2R-methyl-3R-hydroxybutyryl)butyryl]-β-D-quinovopyranosyl-(1->4)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->2)-[O-(4-O-2S-methyl-3S-hydroxybutyryl)-α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranoside 
• 80-59-1 Tiglic acid 
• 90033-09-3 N-(2-t-butyldimethylsiloxyethyl)-2-methylacetoacetamide 
• 34293-67-9 methyl 3-(R)-hydroxy-2-(S)-methylbutanoate 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 27372-03-8 ethyl 3-hydroxy-2-methylbutyrate 

Downstream Products

• 80-59-1 Tiglic acid 
• 7732-18-5 water 
• 84568-00-3 (2R,3S)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Acylated glycosides of hydroxy fatty acid methyl esters generated from the crude resin glycoside (pharbitin) of seeds of pharbitis nil by treatment with indium(III) chloride in methanol

Treatment of the crude ether-insoluble resin glycoside (convolvulin) from seeds of Pharbitis nil (Pharbitis Semen), called pharbitin, with indium(III) chloride in methanol provided seven oligoglycosides of hydroxy fatty acid methyl esters partially acylated by 2-methyl-3-hydroxybutyric (nilic) and 2S-methylbutyric acids. Their structures were elucidated on the basis of NMR and MS data and chemical conversions.

Glycolipid ester-type heterodimers from Ipomoea tyrianthina and their pharmacological activity

Tyrianthins A (1) and B (2), two new partially acylated glycolipid ester-type heterodimers were isolated from Ipomoea tyrianthina. Scammonic acid A was determined as the glycosidic acid in both monomeric units. Tyrianthin A (1) (IC50 0.24 ± 0.0

Iridoid glycosides and grayanane diterpenoids from the roots of Craibiodendron henryi

Four new iridoid glycosides, 10-O-trans-p-coumaroylscandoside (1), 10-O-cis-p-coumaroylscandoside (2), 10-O-trans-p-coumaroyldesacetyl asperulosidic acid (3), and 10-O-cis-p-coumaroyldesacetyl asperulosidic acid (4), and two new grayanane diterpenoids, 14β-O-(2S,3S-nilyl)-2α, 3β,5β,6β,16α-pentahydroxygrayanane (5) and 14β-O-(2S,3S-nilyl)-2α,3β,5β,6β,16α- pentahydroxygrayan-10(20)-ene (6), have been isolated from Craibiodendron henryi. The structures of these compounds were determined by chemical and spectroscopic methods including 1H-1H COSY, HMQC, HMBC, and NOESY experiments. Antioxidant activities and vasodilator effects of these compounds were assessed.

Novel coumarin and chromene compounds and methods of preparation and use thereof for treating or preventing viral infections

The present invention relates to methods of preparation and use of coumarin and chromene compounds for treating or preventing viral infections.

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[ 1,2-b:3,4-b ′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy- 10-propyl-2H,8H-benzo[1,2-b:3,4-b ′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.

CHIRAL PROPIONATE ENOLATE EQUIVALENTS FOR THE STEREOSELECTIVE SYNTHESIS OF THREO- OR ERYTHRO-α-METHYL-β-HYDROXY ACIDS.

The aluminium and copper enolates derived from (n5-C5H5)Fe(CO)(PPh3)COCH2CH3 are chiral propionate enolate equivalents which on reaction with aldehydes (RCHO, R=Me, Et, iPr, tBu) provide stereoselective sytheses of threo-

STEREOSELECTIVE REDUCTION OF 3-OXO AMIDES WITH ZINC BOROHYDRIDE

2-Alkyl-3-oxo amides were reduced to the corresponding syn-2-alkyl-3-hydroxy amides with high stereoselectivity by zinc borohydride.

Methods for the Stereoselective Cis Cyanohydroxylation and Carboxyhydroxylation of Olefins

Two valuable reagents for the cis-specific vicinal cyanohydroxylation and carboxyhydroxylation of olefins are described.The cyanohydroxylation process is based on the decarboxylative ring opening of 3-carboxyisoxazolines prepared by the cycloaddition reaction of carbethoxyformonitrile oxide with various alkenes.Fragmentation of the isoxazolines prepared from cis- and trans-2-butene has been found to occur without any crossover in stereochemistry.The carboxyhydroxylation process begins with the dipolar cycloaddition reaction of the nitrile oxide derived from thetetrahydropyranyl ether derivative of 2-nitroethanol.Deprotection, hydrogenation, and oxitative cleavage of the derived dihydroxy ketone yield the stereochemcally pure β-hydroxy carboxylic acid.