87118-64-7

Basic information

• Product Name: (S)-3-Hydroxyglutaricacidmonomethylester
• Synonyms: (S)-3-Hydroxyglutaricacidmonomethylester
• CAS NO: 87118-64-7
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• Mol File: 87118-64-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-Hydroxyglutaricacidmonomethylester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Hydroxyglutaricacidmonomethylester(87118-64-7)
• EPA Substance Registry System: (S)-3-Hydroxyglutaricacidmonomethylester(87118-64-7)

Safety Data

• Hazardous Substances Data: 87118-64-7(Hazardous Substances Data)

Usage

Description

(S)-3-Hydroxyglutaric acid monomethyl ester, a hydroxy acid derivative of 3-hydroxyglutaric acid, is an important intermediate in the tricarboxylic acid cycle. This chemical compound features a methoxy group attached to the hydroxyl group, which contributes to its potential medicinal properties. Recognized for its role in cellular metabolism and energy production, (S)-3-Hydroxyglutaricacidmonomethylester holds promise for pharmaceutical development to treat various diseases. Its structural and functional attributes render it a valuable compound for research and development in biochemistry, pharmacology, and medicine.

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

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

Relevant articles and documents

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.

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.