473-86-9

Usage

Chemical Properties

Pale orange Oil

Uses

3-Hydroxy-2-methylbutanoic Acid (cas# 473-86-9) is a compound useful in organic synthesis.

Definition

ChEBI: A 3-hydroxy monocarboxylic acid that is butyric acid which is substituted by a methyl group and a hydroxy group at positions 2 and 3, respectively.

InChI:InChI=1/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)

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 
• 27372-03-8 ethyl 3-hydroxy-2-methylbutyrate 
• 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 

Downstream Products

• 80-59-1 Tiglic acid 
• 7732-18-5 water 

Relevant academic research and scientific papers

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

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.