113278-68-5

Basic information

• Product Name: (R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID
• Synonyms: (R)-(-)-2,2-Dimethyl-5-oxo-1,3-dioxolane-4-acetic acid 95%;[(4R)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLAN-4-YL]ACETIC ACID;(R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID;(R)-(-)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic;[(R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic Acid;2-((R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic Acid;(R)-2,2-DiMethyl-5-oxo-;(R)-(-)-2,2-DiMethyl-5-oxo-1,3-dioxolane-4-acetic acid,95%
• CAS NO: 113278-68-5
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• Product Categories: Chiral Reagents;Heterocycles;Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 113278-68-5.mol

Chemical Properties

• Melting Point: 95-98°C
• Boiling Point: 341.4°Cat760mmHg
• Flash Point: 143.7°C
• Appearance: /
• Density: 1.262g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 3.96±0.10(Predicted)
• CAS DataBase Reference: (R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID(113278-68-5)
• EPA Substance Registry System: (R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID(113278-68-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 113278-68-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID is used as an intermediate/starting material for the synthesis of (R)-isoserine, a glucagon receptor antagonist, which has potential applications in the treatment of metabolic disorders such as diabetes and obesity.
Used in Organic Chemistry:
(R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID is used as an optically active inhibitor in various chemical reactions, contributing to the synthesis of complex organic molecules with specific stereochemistry.
Used in Pheromone Production:
(R)-(-)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLANE-4-ACETIC ACID is used as a key component in the production of blepharismone, a pheromone of Blepharisma japonicum, which is utilized in biological research and pest control strategies.

InChI:InChI=1/C7H10O5/c1-7(2)11-4(3-5(8)9)6(10)12-7/h4H,3H2,1-2H3,(H,8,9)/t4-/m1/s1

Upstream product

• 97-67-6 (S)-Malic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 116-11-0 2-Methoxypropene 
• 617-48-1 malic acid 
• 67-64-1 acetone 
• 636-61-3 D-Malic acid 
• 1738-69-8 L-Leucine benzyl ester 
• 174563-88-3 (5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one 

Downstream Products

• 52079-23-9 (3S)-3-hydroxydihydrofuran-2(3H)-one 
• 124724-88-5 (5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one 
• 265659-42-5 7-(1,2-O-isopropylidene-malyl) baccatin III 
• 174563-84-9 (S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate 
• 229032-22-8 (S)-{2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-4-hydroxy-phenyl}-carbamic acid tert-butyl ester 
• 229032-21-7 (S)-{4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-phenyl}-carbamic acid tert-butyl ester 
• 124724-89-6 Benzoic acid 2-((S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-ethyl ester 
• 381234-66-8 C₂₃H₂₈O₅Si 
• 242810-01-1 2-[2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid benzyl ester 
• 1316665-68-5 (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid 4-allyl-2-methoxy-phenyl ester 
• 1402049-31-3 5-{2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-4-(3,5-di-tert-butyl-4-methoxy-phenylsulfanyl)-piperidin-1-yl]-2-oxo-ethyl}-2,2-dimethyl-[1,3]dioxolan-4-one 
• 385836-99-7 (S)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester 
• 1428655-48-4 benzyloxycarbonylmethyl 3β-[(S)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetyloxy]olean-12-en-28-oate 
• 1428655-46-2 benzyl 3β-[(S)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetyloxy]olean-12-en-28-oate 

Relevant articles and documents

Water-soluble prodrugs of paclitaxel containing self-immolative disulfide linkers

A new series of disulfide-containing prodrugs of paclitaxel were designed, synthesized and evaluated against 6 cancer cell lines. Some of these prodrugs exhibited nearly equal or slightly better anticancer activity when compared to that of paclitaxel. These prodrugs contain water-soluble groups such as amino, carboxyl, hydroxyl, amino acids, etc., and exhibited 6-140 fold increase in aqueous solubility when compared to paclitaxel. One of these prodrugs exhibited improved water solubility, better in vitro anticancer activity and significantly superior oral bioavailability in mice when compared to those of paclitaxel. Thus, we have identified a very promising lead compound for further optimization and evaluation as a potentially bioavailable water-soluble prodrug of paclitaxel.

Synthesis of Saxitoxin and Its Derivatives

The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid. The bicyclic guanidine unit was constructed by the intramolecular aminal formation of an acyclic bis-guanidine derivative possessing a ketone carbonyl at C-4. From the bicyclic aminal intermediate, (+)-saxitoxin, (+)-decarbamoyl-β-saxitoxinol [(+)-dc-β-saxitoxinol], and the unnatural skeletal isomer, (-)-iso-dc-saxitoxinol, were synthesized.

Light-triggered intramolecular cyclization in poly(lactic- co -glycolic acid)-based polymers for controlled degradation

Polylactide (PLA) and poly(dl-lactide-co-glycolide) (PLGA) are two prominent FDA-approved polymers because of their useful biodegradation into largely innocuous substances. Their hydrolytic degradation is slow and offers minimal control over degradation kinetics, especially in the minutes time scale. However, molecular engineering of their structures could allow triggered degradation. We have synthesized, by ring-opening polymerization (ROP), a series of PLGA-based polymers containing pendant nucleophiles protected with photocleavable groups. Upon deprotection, two of the polymers degrade rapidly via intramolecular cyclization into small molecules. Nanoparticles formulated from these polymers undergo rapid structural changes in response to UV light. This work introduces a novel polymeric structure to enable rapid on-demand degradation and expands the library of polymers that degrade by cyclization.

A practical synthesis of the major 3-hydroxy-2-pyrrolidinone metabolite of a potent CDK2/cyclin A inhibitor

The synthesis of the major metabolite of a potent 3-aminopyrazole CDK2/cyclin A inhibitor is presented. A stereoconservative approach starting from malic acid was employed to construct the hydroxy-substituted pyrrolidinone moiety. In the key step of the s

Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis

We have analyzed the abundance of bacterial sulfonosphingolipids, including rosette-inducing factors (RIFs), in seven bacterial prey strains by using high-resolution tandem mass spectrometry (HRMS2) and molecular networking (MN) within the Glob

A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

Preparation method of alpha-hydroxyl-gamma-butyrolactone

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of alpha-hydroxyl-gamma-butyrolactone. The method is characterized in that malic acid is used as a raw material, and alpha-hydroxyl-gamma-butyrolactone is synthesized with high yield through four steps of reactions, namely, carboxyl and alpha-hydroxyl protection, beta-carboxyl reduction, protecting group removal and internal esterification. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of alpha-hydroxy-gamma-butyrolactone.

L-malic acid dimer impurity and preparation method thereof

The invention provides an L-malic acid dimer impurity and a preparation method thereof. The L-malic acid dimer impurity (impurity X) is discovered and separated for the first time, and has a structureshown in the specification. The preparation method of the impurity X comprises the following steps: (1) protecting a carboxyl group at one side of L-malic acid to obtain a compound 1; (2) protectinga carboxyl group at the other side of the compound 1 to obtain a compound 2; (3) hydrolyzing the compound 2 under the condition of acetic acid/water/tetrahydrofuran to obtain a compound 3; (4) dehydrating and condensing the compound 3 to obtain a compound 4; and (5) hydrogenating the compound 4 to remove benzyl groups to obtain the impurity X. The impurity spectrum of malic acid stability researchis expanded, and the improvement of the malic acid quality standard is promoted. The compound property of the L-malic acid dimer impurity is studied, and the L-malic acid dimer impurity has positiveguiding significance for selection of storage conditions of malic acid.

Synthesis and structure reassignment of malylglutamate, a recently discovered earthworm metabolite

Malylglutamate, a newly identified metabolite in earthworms, was synthesized using a traditional peptide coupling approach for assembling the amide from protected malate and glutamate precursors. The proposed structure (1) and a diastereomer were synthesized, but their NMR spectra did not match the natural sample. Further analysis of the natural sample using HMBC spectroscopy suggested an alternative attachment of the malyl moiety, and β-malylglutamate (2) diastereomers were synthesized, L,L-2 and D,D-2. NMR spectra were an excellent match with the natural sample, and chiral-phase chromatography was employed to identify (a)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.

STIMULUS-RESPONSIVE POLY(LACTIC-CO-GLYCOLIC)-BASED POLYMERS AND NANOPARTICLES FORMED THEREFROM

PLGA-based polymers include pendant nucleophiles protected with photocleavable protecting groups. Upon deprotection, the polymers degrade rapidly via intramolecular cyclization into small molecules. The polymer may be formulated as a nanoparticle, with an encapsulated payload, which may be an imaging agent, a bioactive agent or a pharmaceutical agent.