52373-72-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER is used as a starting material for the preparation of matrix metalloproteinases (MMP) inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, such as cancer, where MMPs are involved in tumor growth, invasion, and metastasis.
Used in Research and Development:
In the field of research, (R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER serves as a starting material to synthesize (2R)-[1-2H2]-glycerol. This probe is essential for studying the stereochemistry of glycerol metabolism in Streptomyces cattleya, a bacterium known for its ability to produce various bioactive compounds.
Used in Organic Synthesis:
(R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER is also utilized as a building block in the synthesis of various organic compounds. Two examples include (R)-2,3-dihydroxy-3-methylbutyl toluene-p-sulfonate and (2S,8R)-2-amino-8-[(R) 2,2-dimethyl-1,3-dioxolan-4-yl]-8-oxooctanoic acid. These compounds can be used in the development of new pharmaceuticals, agrochemicals, or other specialty chemicals.

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

Upstream product

• 67-56-1 methanol 
• 14028-61-6 potassium (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 18289-89-9 methyl (2R)-2,3-dihydroxypropanoate 
• 67-64-1 acetone 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 83400-91-3 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid potassium salt 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 615-34-9 methyl glycerate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 

Downstream Products

• 82268-15-3 2-<(R)-2,2-dimethyl-1,3-dioxolane-4-yl>-2-propanol 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 85364-10-9 2-chloro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone 
• 67-56-1 methanol 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 343783-13-1 dibenzyl {2-[(1R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxoethyl}phosphonate 
• 286845-22-5 1-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-(4-trifluoromethoxyphenoxy)phenylsulfonyl)ethanone 
• 288162-71-0 (R)-2-Benzyloxymethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 171775-72-7 (R)-N-benzyl 2,2-dimethyl-1,3-dioxolane-4-carboxamide 
• 91190-38-4 N-benzyl-1,2-O-isopropylidene-D-glyceraldehyde nitrone 
• 56017-85-7 (S)-4-ethynyl-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

An Esterase-like Lyase Catalyzes Acetate Elimination in Spirotetronate/Spirotetramate Biosynthesis

Spirotetronate and spirotetramate natural products include a multitude of compounds with potent antimicrobial and antitumor activities. Their biosynthesis incorporates many unusual biocatalytic steps, including regio- and stereo-specific modifications, cyclizations promoted by Diels–Alderases, and acetylation-elimination reactions. Here we focus on the acetate elimination catalyzed by AbyA5, implicated in the formation of the key Diels–Alder substrate to give the spirocyclic system of the antibiotic abyssomicin C. Using synthetic substrate analogues, it is shown that AbyA5 catalyzes stereospecific acetate elimination, establishing the (R)-tetronate acetate as a biosynthetic intermediate. The X-ray crystal structure of AbyA5, the first of an acetate-eliminating enzyme, reveals a deviant acetyl esterase fold. Molecular dynamics simulations and enzyme assays show the use of a His-Ser dyad to catalyze either elimination or hydrolysis, via disparate mechanisms, under substrate control.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

A Native Ternary Complex Trapped in a Crystal Reveals the Catalytic Mechanism of a Retaining Glycosyltransferase

Glycosyltransferases (GTs) comprise a prominent family of enzymes that play critical roles in a variety of cellular processes, including cell signaling, cell development, and host-pathogen interactions. Glycosyl transfer can proceed with either inversion

Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (Di)acids

A new method to accomplish glycol cleavage to carboxylic (di)acids in one step using catalytic amounts of tetrapropylammonium perruthenate (TPAP) together with N-methylmorpholine N-Oxide (NMO) as the stoichiometric oxidant is presented. In addition to regenerating the active catalyst, the N-oxide stabilizes intermediary carbonyl hydrates and thereby shifts a crucial equilibrium. The mild oxidation protocol is applicable to a broad range of substrates providing the respective acids, diacids, or keto acids in high yields.

d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3

d- and l-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)2-D3, 24R,25-(OH)2-D3 and 1α,24R,25-(OH)3-D3.

Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane) , was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol%) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium-(III)-DIANANE complex.

PROCESS FOR THE ENZYMATIC RESOLUTION OF 1,3-DIOXOLANE-4-CARBOXYLATES

The present invention relates to enzymatic' resolution of enantiomeric mixtures of 1,3-dioxolane-4-carboxylate esters of Formula I. More particularly, the present invention relates to a process for preparing R and S enantiomers of methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate in high optical purity.

Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-D-glyceric acid (1,3-diPG) analogues

Various phosphono-phosphates and diphophonates were synthesized as 1,3-diphosphoglycerate 1,3-diPG) analogues by using a β-ketophosphonate, an α-fluoro,β-ketophosphonate or a β-ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural

A β-lactam-based stereoselective access to β,γ-dihydroxy α-amino acid-derived peptides with either α,β-like or unlike configurations

A concise access to α,β-dihydroxy α-amino acid-derived N-carboxy anhydrides (NCAs) with either like or unlike relative configuration is described. The key steps of the synthetic route are the preparation of the nonracemic 4-alkenyl β-lactams, through either Homer-type olefination of a common 4-formyl β-lactam or the Corey-Winter alkene synthesis applied to 4-dihydroxyalkyl β-lactams, followed by the Sharpless AD reaction, and a subsequent ring expansion of the corresponding 4-substituted 3-hydroxy β-lactams promoted by TEMPO. The opening of thus-prepared NCAs upon treatment with different O- and N-nucleophiles, including α-amino esters which lead to peptides, has also been studied under various reaction conditions.

Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities

We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (VHR, cdc25A, cdc25B, and PPI) are also reported.