33204-46-5

Usage

Uses

Used in Chemical Processes:
(2S)-2-METHYL-1,2-BUTANEDIOL is used as a solvent for various chemical processes due to its ability to dissolve a wide range of substances and its compatibility with different reaction conditions.
Used in Pharmaceutical Synthesis:
(2S)-2-METHYL-1,2-BUTANEDIOL is used as a precursor in the synthesis of pharmaceuticals and other organic compounds, taking advantage of its chiral properties to produce enantiomerically pure products.
Used in Fragrance and Flavor Production:
(2S)-2-METHYL-1,2-BUTANEDIOL is used in the production of fragrances and flavors, where its unique properties contribute to the creation of distinct scents and tastes.
Used in Asymmetric Synthesis:
(2S)-2-METHYL-1,2-BUTANEDIOL is used as a reagent in asymmetric synthesis, where its chiral nature allows for the selective formation of specific enantiomers, which are important in the development of pharmaceuticals and other chiral compounds.

Upstream product

• 917-54-4 methyllithium 
• 55058-23-6 (2R/3R)/(2S,3S)-2,3-epoxy-butanol 
• 81286-85-3 (2S,5R)-2-(tert-butyl)-5-ethyl-5-methyl-1,3-dioxolan-4-one 
• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 80-59-1 Tiglic acid 
• 72447-47-3 (-)-menthyl (Z)-2-methyl-2-butenoate 

Downstream Products

• 55033-09-5 Benzoic acid (S)-2-hydroxy-2-methyl-butyl ester 
• 1354575-59-9 (3S,9S)-9-((4-methoxybenzyl)oxy)-9-methyl-8-oxoundec-1-en-3-yl acrylate 
• 1354575-82-8 C₂₀H₃₀O₄ 
• 1354575-81-7 C₂₀H₂₉IO₄ 
• 1354575-78-2 C₁₃H₁₈O₃ 
• 1354575-62-4 (3R,9R)-9-((4-methoxybenzyl)oxy)-9-methyl-8-oxoundec-1-en-3-yl acrylate 
• 1354575-85-1 C₂₀H₃₀O₄ 
• 1354575-84-0 C₂₀H₂₉IO₄ 
• 1354575-61-3 (R)-8-((2R,3R)-3-(hydroxymethyl)oxiran-2-yl)-3-((4-methoxybenzyl)oxy)-3-methyl-octan-4-one 
• 1354575-54-4 (3S,9R)-9-((4-methoxybenzyl)oxy)-9-methyl-8-oxoundec-1-en-3-yl acrylate 
• 1354575-76-0 C₂₀H₃₀O₄ 
• 1354575-75-9 C₂₀H₂₉IO₄ 
• 1354575-49-7 (R)-8-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-3-((4-methoxybenzyl)oxy)-3-methyl-octan-4-one 
• 1354575-53-3 (R,E)-11-hydroxy-3-((4-methoxybenzyl)oxy)-3-methylundec-9-en-4-one 

Relevant academic research and scientific papers

The absolute configuration of cuauhtemone and related compounds

The absolute configuration of cuauhtemone, a eudesmane-type sesquiterpene isolated from Pluchea species (Asteraceae), has been revised from 1 to 2 by chemical correlation with (R)-(+)-2-methyl-1,2-butanediol 3 through the naturally occurring 2,3-epoxy-2-methylbutanoate derivative 4. The relative stereochemistry of 4 was confirmed by X-ray diffraction analysis. The obtained data are also useful for reconsideration of the absolute configurations of a relevant group of natural products, which were elucidated according to the stereochemistry of cuauhtemone.

Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis

The first total synthesis of extracellular factor, Avenolide, in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4S,10R, and yielded important information on its structure-activity relationship.

The absolute configuration and total synthesis of korormicin

The marine antibiotic korormicin, isolated from the culture filtrate of marine bacterial strain Pseudoalteromonas sp. F-420, specifically inhibits the growth of marine Gram-negative bacteria without affecting terrestrial species. The absolute configuration of korormicin was determined by the combination of a CD exciton chirality method and chemical degradation. Convergent total synthesis of korormicin has been also achieved.

Enantioselective preparation of (2R,3R)-(+)- and (2S,3S)-(-)-2,3-epoxy- 2-methylbutanoic acids and some derivatives

(2R,3R)-(+)- and (2S,3S)-(-)-2,3-epoxy-2-methylbutanoic acids (epoxyangelic acids) were prepared from (Z)-2-methyl-2-butenoic acid using the Sharpless asymmetric epoxidation method in combination with the use of (- )- and (+)-menthol as chiral auxiliaries. Both substances, obtained in high enantiomeric excess, were characterized by spectroscopic and optical activity data. Their absolute configuration was determined by correlation with (R)- (+)-2-methyl-1,2-butanediol.

Preparation of (2R,3S)-(-)- and (2S,3R)-(+)-2,3-Epoxy-2-methylbutanoic Acids and Some of Their Esters

Enantiomerically pure (2R,3S)-(-)- and (2S,3R)-(+)-2,3-epoxy-2-methylbutanoic acids 7 and 8 were prepared from 2-methyl-2-butenoic acid 1 (tiglic acid).They were characterized by spectroscopic and optical activity data and their absolute configuration was determined by chemical correlation with (R)-(+)- and (S)-(-)-2-methyl-1,2-butanediols.The corresponding methyl (16 and 17), menthyl (3 and 4), and 9α-angeloyloxy-1-oxolongipin-2-en-7β-yl (14 and 15) esters were also prepared.

Intermediates for preparing optically active carboxylic acids

A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula STR1 in which the substituents have the meaning given in the description of the invention.

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).