63473-60-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-METHYL HYDROGEN 3-METHYLGLUTARATE is used as a chiral building block for the synthesis of pharmaceuticals, leveraging its unique stereochemistry to create enantiomerically pure compounds that can interact specifically with biological targets, thus enhancing the efficacy and safety of drugs.
Used in Chemical Research:
In the realm of chemical research, (R)-1-METHYL HYDROGEN 3-METHYLGLUTARATE serves as an important compound for studying reaction mechanisms, exploring asymmetric synthesis, and developing new methodologies for the preparation of enantiomerically pure molecules.
Used in Organic Synthesis:
(R)-1-METHYL HYDROGEN 3-METHYLGLUTARATE is utilized as a key intermediate in organic synthesis for the production of various industrial chemicals, taking advantage of its reactive functional groups to form a wide range of derivative compounds with diverse applications.
Used in Drug Development:
As a scaffold in drug development, (R)-1-METHYL HYDROGEN 3-METHYLGLUTARATE is employed for the design and synthesis of new bioactive compounds, potentially leading to the discovery of innovative treatments for various diseases and conditions.

InChI:InChI=1/C7H12O4/c1-5(3-6(8)9)4-7(10)11-2/h5H,3-4H2,1-2H3,(H,8,9)/t5-/m1/s1

Upstream product

• 27151-65-1 3-methyl-1,5-pentanedioic acid monomethyl ester 
• 19013-37-7 dimethyl 3-methylglutarate 
• 108330-16-1 (S)-3-Methyl-pentanedioic acid tert-butyl ester methyl ester 
• 67-56-1 methanol 
• 160204-85-3 (3R)-3-Methylglutaric acid 1-<(R)-mandelic acid> ester 
• 4166-53-4 3-methylglutaric anhydride 
• 128217-53-8 (E,Z)-methyl 5-(benzyloxy)-2-pentenoate 
• 68702-74-9 (S)-methyl5-hydroxy-3-methylpentanoate 
• 626-51-7 3-methyl glutaric acid 
• 1753-40-8 (R)-4-menthen-3-one 
• 65844-74-8 2-methylpropan-1,1,3-tricarboxylic acid trimethyl ester 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 108330-09-2 (+)-3-phenylselenomethyl glutaric acid methyl t-butyl mixed diester 
• 43080-04-2 3-(S)-methylpentanedioic acid mono-tert-butyl ester 

Downstream Products

• 65781-38-6 D-3-methyl-undecanoic acid 
• 13490-36-3 D-3-methyl-dodecanoic acid 
• 101577-55-3 (R)-3-methyl-octanedioic acid-8-benzyl ester-1-methyl ester 
• 61898-55-3 (4R)-4-methyltetrahydro-2H-pyran-2-one 
• 61898-56-4 (S)-4-methyltetrahydro-2H-pyran-2-one 
• 763906-32-7 (R)-4-[(E)-(1S,2S)-2-(3,4-Dichloro-benzyl)-1-methyl-4-naphthalen-2-yl-but-3-enylcarbamoyl]-3-methyl-butyric acid methyl ester 
• 60660-35-7 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid 
• 116415-49-7 (R)-3,9-dimethyl 5-oxo (R,S)-6-phenylsulfonyl 8-decen 1-ol 
• 116415-51-1 2-(1-Benzenesulfonyl-4-methyl-pent-3-enyl)-4-methyl-tetrahydro-pyran-2-ol 
• 116415-56-6 1-t-butyldimethylsilyloxy (S)-3,9-dimethyl 6-phenylsulfonyl (E)-5,8-decadiene 
• 116415-52-2 1-t-butyldimethylsilyloxy (R)-3,9-dimethyl (R,S)-6-phenylsulfonyl 8-decen 5-one 
• 116415-54-4 1-t-butyldimethylsilyloxy (R)-3,9-dimethyl (R,S)-6-phenylsulfonyl 8-decen (R,S)-5-ol 
• 116415-55-5 1-t-butyldimethylsilyloxy (R)-3,9-dimethyl (R,S)-6-phenylsulfonyl 8-decen (R,S)-5-yl acetate 
• 16958-25-1 (R)-3-methylpentanoic acid 

Relevant academic research and scientific papers

ENZYMES IN ORGANIC SYNTHESIS. 42. INVESTIGATION OF THE EFFECTS OF THE ISOZYMAL COMPOSITION OF PIG LIVER ESTERASE ON ITS STEREOSELECTIVITY IN PREPARATIVE-SCALE ESTER HYDROLYSES OF ASYMMETRIC SYNTHETIC VALUE.

The stereospecificities of the isozyme components of commercially available pig liver esterase have been shown to be essentially the same toward representative monocyclic and acyclic diester substrates. This removes previous concerns that the isozymal com

ASYMMETRIC RING OPENING OF CYCLIC ACID ANHYDRIDES WITH LIPASE IN ORGANIC SOLVENTS

A lipase (Amano P) catalyzed the asymmetric ring opening of 3-substituted glutaric anhydride with 1-butanol to afford the R half esters having 60-91percentee.

Cinchona alkaloid derivative modified Fe3O4nanoparticles for enantioselective ring opening of: Meso -cyclic anhydrides

In the present work, the molecular framework of quinidine was modified at the methoxy functional group of the C6′ carbon of the quinoline moiety with a long-chain carboxylic acid group (-COOH) and it was used as a capping agent during the synthesis of Fe3

Synthesis of a CGRP Receptor Antagonist via an Asymmetric Synthesis of 3-Fluoro-4-aminopiperidine

A practical and efficient enantioselective synthesis of the calcitonin gene-related peptide receptor antagonist 1 has been developed. The key structural component of the active pharmaceutical ingredient is a syn-1,2-amino-fluoropiperidine 4. Two approaches were developed to synthesize this important pharmacophore. Initially, Ru-catalyzed asymmetric hydrogenation of fluoride-substituted enamide 8 enabled the synthesis of sufficient quantities of compound 1 to support early preclinical studies. Subsequently, a novel, cost-effective route to this intermediate was developed utilizing a dynamic kinetic asymmetric transamination of ketone 9. This synthesis also features a robust Ullmann coupling to install a bis-aryl ether using a soluble Cu(I) catalyst. Finally, an enzymatic desymmetrization of meso-diester 7 was exploited for the construction of the γ-lactam moiety in 1.

Atropselective Synthesis of N,C-Bis(diphenylphosphanes) from Bridged 2-Arylindoles Based on Effective Point-to-Axial Asymmetric Inductions after an Unusual Dilithiation ⊥

An asymmetric methanolysis of glutaric anhydride and 6 ensuing steps gave veratrol-annulated dimethylcyclo-heptenone diastereomers with 99% ee; ring closures occurred by Friedel-Crafts acylations of carboxylic acids obtained by stereospecific hydrogenolyses of a pair of diastereomeric δ-lactones. The mentioned cycloheptenones and Ph-NH-NH2 underwent Fischer indole syntheses providing the tetracyclic indoles cis- and trans-14a, respectively. Double lithiations with BuLi and quenchings with ClPPh2 furnished the diphosphanes cis- and trans-15 with perfect (P)- and (M)-atropselectivity, respectively.

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

Enantioselective acyl-transfer catalysis by fluoride ions

The asymmetric nucleophilic catalysis by fluoride ions at a carbon-based electrophile has been demonstrated for the first time. Using a library of ad hoc designed bifunctional phase-transfer catalysts in which both the anion and the cation are directly involved in the reaction, the desymmetrisation of meso-succinic and -glutaric anhydrides is possible.19F NMR spectroscopic studies support the intermediacy of an acyl fluoride intermediate.

Toward the total synthesis of patellazole B: Synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton

The patellazoles are a family of complex marine macrolides that exhibit potent cytotoxicity against cancer cell lines. However, despite extensive characterisation efforts, their full stereochemical assignment has remained elusive. We report our approach towards the synthesis-enabled structural elucidation of patellazole B (4), a 24-membered macrolide with 16 stereocentres and a signature thiazole-containing side chain. Our plan hinges upon isolating the unknown stereocentres into a single C20-C25 fragment to facilitate the flexible assembly of various possible diastereomers of an advanced C1-C25 fragment. Towards this end, a highly convergent and modular synthesis of one candidate diastereomer 37, corresponding to the patellazole B macrocyclic skeleton, has been achieved based on the strategic application of stereocontrolled aldol methodology, combined with Suzuki and Heck cross-coupling reactions.

Toward aplyronine payloads for antibody-drug conjugates: Total synthesis of aplyronines A and D

The aplyronines are a family of antimitotic marine macrolides that disrupt cytoskeletal dynamics by dual targeting of both actin and tubulin. Given their picomolar cytotoxicity profile and unprecedented mode of action, the aplyronines represent an excellent candidate as a novel payload for the development of next-generation antibody-drug conjugates (ADCs) for cancer chemotherapy. Enabled by an improved second-generation synthesis of the macrolactone core 5, we have achieved the first total synthesis of the most potent congener aplyronine D together with a highly stereocontrolled synthesis of aplyronine A. To facilitate step economy, an adventurous site-selective esterification of the C7 hydroxyl group was performed to install the N,N,O-trimethylserine pharmacophore to directly afford aplyronines A and D. Toward the assembly of ADCs incorporating an aplyronine warhead, the C29-ester derivative 4 featuring an Fmoc-amino substituted linker attached to the actin-binding tail region was also prepared by adapting this flexible endgame.

Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides

The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S,2R)-12 a–f and (1R,2R)-15 a–c, and their use in the enantioselective alcoholysis of meso-anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)-12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)-15 a–c. This technique was used to synthesize (R)-(?)-baclofen.