19013-37-7

Usage

Uses

Used in Pharmaceutical Industry:
DIMETHYL 3-METHYLGLUTARATE is used as a synthetic intermediate for the production of (R)and (S)-4-amino-3-methylbutanoic acids. These amino acids are essential in the development of pharmaceuticals, as they are involved in various biological processes and can be used to treat specific medical conditions.
Used in Perfumery:
DIMETHYL 3-METHYLGLUTARATE is used as a building block for the synthesis of (R,Z)-muscenone, an important ingredient in the perfume industry. Its unique scent profile contributes to the creation of various fragrances, making it a valuable component in the formulation of perfumes and colognes.
Used in Enzymatic Synthesis:
DIMETHYL 3-METHYLGLUTARATE is used as a substrate in enantioselective hydrolysis with pig liver esterase, a process that allows for the preparation of optically active compounds, such as verrucarinic acid derivatives. These optically active compounds have potential applications in various fields, including pharmaceuticals and agrochemicals.
Used in Chemoenzymatic Asymmetric Synthesis:
DIMETHYL 3-METHYLGLUTARATE serves as a crucial building block in chemoenzymatic asymmetric synthesis, a technique that combines chemical and enzymatic reactions to produce chiral compounds with high enantioselectivity. This method is widely used in the synthesis of complex molecules, such as pharmaceuticals and natural products, where the stereochemistry of the molecule is crucial for its biological activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 2132, 1994 DOI: 10.1021/jo00087a033Tetrahedron Letters, 26, p. 5643, 1985 DOI: 10.1016/S0040-4039(01)80908-4

InChI:InChI=1/C8H14O4/c1-6(4-7(9)11-2)5-8(10)12-3/h6H,4-5H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 626-51-7 3-methyl glutaric acid 
• 67030-12-0 3-methylpentanedioyl dichloride 
• 41527-39-3 dimethyl (2E)-pent-2-enedioate 
• 676-58-4 methylmagnesium chloride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 65844-74-8 2-methylpropan-1,1,3-tricarboxylic acid trimethyl ester 
• 623-43-8 crotonic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 88192-98-7 myxopyronin A 
• 1753-40-8 (R)-4-menthen-3-one 
• 5164-76-1 dimethyl glutaconate 
• 82538-51-0 (R)-5,5-dimethoxy-3-methylpentanoic acid methyl ester 
• 1427207-34-8 (4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one 

Downstream Products

• 4457-71-0 3-methylpentane-1,5-diol 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 
• 2163-42-0 2-methyl-1.3-propanediol 
• 912293-10-8 C₂₀H₃₆O₄SSi 
• 912293-20-0 C₁₄H₂₂O₄S 
• 912293-11-9 C₁₄H₂₀O₄S 
• 912293-21-1 C₁₅H₂₄O₄S 
• 912293-12-0 C₁₅H₂₂O₄S 
• 853644-39-0 toluene-4-sulfonic acid 5-(4-cyano-phenoxy)-3-methyl-pentyl ester 
• 148054-23-3 3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate) 
• 708208-66-6 4-[3-methyl-5-(2-oxo-3-pyridin-4-yl-imidazolidin-1-yl)-pentyloxy]-benzonitrile 
• 1027529-98-1 toluene-4-sulfonic acid 3-methyl-5-[4-(2-methyl-2H-tetrazol-5-yl)-phenoxy]-pentyl ester 
• 866750-97-2 toluene-4-sulfonic acid 5-(4'-chloro-biphenyl-4-yloxy)-3-methyl-pentyl ester 

Relevant academic research and scientific papers

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.

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.

Preparation method of high-purity and high-yield monomethyl 3-methylglutarate

The invention relates to a preparation method of high-purity and high-yield monomethyl 3-methylglutarate, and belongs to the field of organic synthesis. The preparation method comprises the followingsteps of (1) esterification reaction: performing esterification reaction on beta-methylglutaric acid and methyl alcohol to obtain beta-dimethyl methylglutarate; (2) alkaline hydrolysis reaction: adding a barium hydroxide methyl alcohol solution into the obtained beta-dimethyl methylglutarate to generate barium salt of the monomethyl 3-methylglutarate; (3) finished product preparation: performing hydrochloric acid acidification, diethyl ether extraction and rectification and purification on the barium salt of the monomethyl 3-methylglutarate to obtain the monomethyl 3-methylglutarate. The prepared monomethyl 3-methylglutarate has the advantages of high yield, high purity and high mono-esterification selectivity. The preparation method is scientific and reasonable; simplicity is realized; the implementation is easy; the method is suitable for industrial mass production.

Method for synthesizing muscone by utilizing beta-monomethyl methylglutarate

The invention discloses a method for synthesizing muscone by utilizing beta-monomethyl methylglutarate. According to the method, beta-monomethyl methylglutarate and alpha,omega-dodecanedioic acid monomethyl ester respectively prepared through a heteropoly acid catalytic transesterification method are used as raw materials, and Kolbe electrolysis, acyloin condensation and reduction reaction are performed to prepare the muscone. The method of the present invention has advantages of high raw material utilization rate, mold condition, easy control and environmental protection, and is suitable for industrial production .

Two potent OXE-R antagonists: Assignment of stereochemistry

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed by the oxidation of 5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-HETE), which is a major metabolite of enzymatic oxidation of arachidonic acid (AA). 5-Oxo-ETE is the most potent lipid chemoattractant for human eosinophils. Its actions are mediated by the selective OXE receptor, which is therefore an attractive target in eosinophilic diseases such as allergic rhinitis and asthma. Recently, we have reported two excellent OXE receptor antagonists that have IC50 values at low nanomolar concentrations. Each of these antagonists has a chiral center, and the isolation of the individual enantiomers by chiral high-performance liquid chromatography (HPLC) revealed that in each case one enantiomer is over 300 times more potent than the other. To unambiguously assign the stereochemistry of these enantiomers and to provide access to larger amounts of the active compounds for biological testing, we report here their total synthesis.

(4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one in the synthesis of polyfunctional compounds with the methyl-branched carbon skeleton

A simple and efficient asymmetrical synthesis was performed of a convenient bifunctional building block, methyl (R)-5,5-dimethoxy-3-methylpentanoate and its (S)-enantiomer. The possibility was shown of its application to the synthesis of insect pheromones.

Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy) alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives

A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.

Chemical compounds

Compound of formula (I) wherein: A is a bicyclic heteroaryl, optionally substituted with one or more substituents; B is linker group connecting group A to group D and comprising a 3 or 4 atom linker where each atom is independently selected from carbon, oxygen, nitrogen and sulphur and is optionally subsituted with one or more C1-6alkyl groups or two of such adjacent alkyl substituents may form a ring; C is aryl or a mono or bicyclic heteroaryl, each of which can be optionally substituted; D is an aryl or heteroaryl, both of which are optionally substituted R1is hydrogen, C1-5alkyl, C1-3alkanoyl or C1-3alkoxycarbonyl; R2to R5are each independently selected from hydrogen, C1-6alkyl, aryl and heteroaryl containing up to 2 heteroatoms chosen from oxygen, sulphur and nitrogen, the aryl and heteroaryl optionally substituted with C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-4alkoxy, C1-4alkanoyl, C1-6alkylamino, C1-4alkylC1-6alkyoxyl, C1-6alkylaminoC1-6alkyl, nitro, cyano, halogeno, trifluoromethyl, hydroxy, (CH2)pOH where p is 1 or 2, —CO2Ra, and —CONRaRb, where Raand Rbare independently selected from hydrogen and C1-6alkyl or two of R2to R5can be taken together to form a 3 to 7 membered ring; R6is an acidic functional group; r and s are each independently 0 or 1 with the proviso that r and s cannot both be 0; or a pharmaceutically acceptable salt or in vivo hydrolysable derivative thereof.

Ozonolytic decyclization of (R)-4-menthen-3-one

Ozonolytic decyclization of (R)-4-menthen-3-one is accompanied by fragmentation of the isobutyl group, leading to ω-functionalized 3-methylpentanoic acid derivatives.

Bucky ligands: Synthesis, Ruthenium(II) complexes, and electrochemical properties

The novel tridentate 2,2':6',2-terpyridine ligand (1) in which the metal-binding domain is directly attached to a methanofullerene C60 unit was incorporated into ruthenium-based diads and triads that may undergo photoinduced charge s