87118-64-7

Usage

Uses

Used in Pharmaceutical Development:
(S)-3-Hydroxyglutaricacidmonomethylester is used as an intermediate in the tricarboxylic acid cycle for its potential role in the development of pharmaceuticals targeting various diseases. Its involvement in cellular metabolism and energy production makes it a promising candidate for therapeutic applications.
Used in Biochemical Research:
In the field of biochemistry, (S)-3-Hydroxyglutaricacidmonomethylester is used as a subject of study to understand its structural and functional properties, which can contribute to the advancement of knowledge in cellular metabolism and energy production.
Used in Medical Research:
(S)-3-Hydroxyglutaricacidmonomethylester is utilized as a compound of interest in medical research, where its potential medicinal properties are explored for the treatment of various diseases and conditions related to cellular metabolism and energy production.

Upstream product

• 7250-55-7 dimethyl 3-hydroxypentanedioate 
• 90613-44-8 methyl 3-acetoxypentanedioate 
• 109721-08-6 (S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester 

Downstream Products

• 87118-68-1 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-(2-tert-butylsulfanylcarbonylmethyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 87138-45-2 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-(2-carboxymethyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 87118-67-0 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-6-tert-butylsulfanylcarbonyl-5-oxo-hexanoic acid methyl ester 
• 87118-69-2 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(2-hydroxy-ethyl)-[1,3]dioxolan-2-yl]-butyric acid methyl ester 
• 87118-66-9 (S)-((3-tert-butyldiphenylsillyl)oxy)pentanedioic acid monomethyl ester 
• 87118-71-6 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{2-[(E)-3-(diisopropoxy-phosphoryl)-allyl]-[1,3]dioxolan-2-yl}-butyric acid methyl ester 
• 87118-74-9 (6E,8E,10E,12E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-5-oxo-hexadeca-6,8,10,12-tetraenoic acid methyl ester 
• 87118-72-7 (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester 
• 87118-70-5 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(2-oxo-ethyl)-[1,3]dioxolan-2-yl]-butyric acid methyl ester 

Relevant academic research and scientific papers

Synthesis of (-)-streptenol A, (±)-streptenol B, C and D

2-(2,2-Dimethyl-1,3-dioxan-4-yl)acetaldehyde (3) was used for the preparation of streptenol A and B (Scheme 1) via a Grignard reaction with 1-bromopent-3-ene. Hereby optically pure (4′R)-3 gave the antipode of Streptenol A. Reaction with lithiated 1-pentyne opened access to streptenol C and D. To obtain the dienone structure of streptenol C and D, a palladium-catalyzed alkynone isomerization was induced. Kinetic differences in the acid-mediated cleavage of the 1,3-acetonide protected 1,3,5-triol system caused the stereoselectivity in the natural products. So only the (3S*,5R*) acetonide of streptenol B reacted under mild hydrolytic conditions and gave after transacetalization first a 3,5-protected streptenol B with pure relative stereochemistry and finally (3S*, 5R*)-streptenol B. VCH Verlagsgesellschaft mbH, 1996.

3-SUBSTITUTED OXYGLUTARIC DIESTER COMPOUND, OPTICALLY ACTIVE 3-SUBSTITUTED OXYGLUTARIC MONOESTER COMPOUND, AND PROCESSES FOR PRODUCING THESE

The present invention is to provide a 3-substituted oxyglutaric acid diester compound represented by the following formula (I):???wherein R1 may be the same or different from each other, and represents a substituted or unsubstituted alkyl group

Synthesis of Novel HMG-CoA Reductase Inhibitors, I Naphthalene Analogs of Mevinolin

The title compounds 2 and their corresponding (6S) epimers 18 are prepared in several steps by starting with chiral formyl ester 5, and α-tetralones 10: (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13, (2) reduction to the corresponding alcohol 14, (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17, and (4) lactonization.This procedure is also used to synthesize the β-naphthyl analogs 29 and 30.Some results obtained from HMG-CoA reductase inhibitor screening are also reported. Key Words: HMG-CoA reductase inhibitors / Naphthylacetates / Pig liver esterase / Glutarate, 3-hydroxy / Lactones

CHEMOENZYMATIC SYNTHESIS OF A C5-CHIRAL BUILDING BLOCK: A SUBSTRATE MODIFICATION APPROACH.

The enantioselectivity of α-chymotrypsin hydrolysis of prochiral dimethyl-3-hydroxyglutarates was contrilled by the proper choice of the hydroxyl protecting groups.This strategy allows the synthesis of a versatile C5-chiral building block.

3-Hydroxyglutarate and β,γ-Epoxy Esters as Substrates for Pig Liver Esterase (PLE) and α-Chymotrypsin

The pH dependence of the α-chymotrypsin-catalyzed hydrolysis of dimethyl 3-hydroxyglutarate (3) has been studied.The e.e. was determined by HPLC analysis of diastereoisomeric camphanoic-acid derivatives.Kinetic resolution of the β,γ-epoxy esters 10 and 24 by pig liver esterase has been shown to provide an alternative access to chiral β-hydroxy esters and acids of high optical purity.By this latter method, the unnatural enantiomer of γ-amino-β-hydroxybutyric acid (GABOB) has been sinthesized.Finally, dimethyl meso-3,4-epoxyadipate (19) was hydrolyzed by pig liver esterase with almost 100 percent selectivity.

Process for preparing optically-active 4-amino-3-hydroxybutyric acid

The present invention relates to processes for preparing optically-active 4-amino-3-hydroxybutyric acid by asymmetrically cleaving one of the enantiotopic ester groupings of 3-hydroxyglutaric diester by the action of microbial enzymes to obtain a chiral monoacid which is readily converted into optically-active 4-amino-3-hydroxybutyric acid by chemical means.

A CONVERGENT SYNTHETIC STRATEGY FOR THE POLYENE MACROLIDE PIMARICIN

The synthesis of two chiral fragments representing C1-11 and C12-25 of the polyene macrolide pimaricin from dimethyl 3-hydroxyglutarate is described.