52373-72-5

Basic information

• Product Name: (R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER
• Synonyms: (R)-METHYL-O-ISOPROPYLIDENE GLYCERATE;(R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER;(R)-2,2-DIMETHYL-[1,3]DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER;(+)-2,3-O-ISOPROPYLIDENE-D-GLYCERIC ACID METHYL ESTER;ALPHA,BETA-ISOPROPYLIDENE-D-GLYCERIC ACID METHYL ESTER;(+)-METHYL 2,3-O-ISOPROPYLIDENE-D-GLYCERATE;METHYL 2,3-O-ISOPROPYLIDENE-D-GLYCERATE;METHYL ALPHA, BETA-ISOPROPYLIDENE-D-GLYCERATE
• CAS NO: 52373-72-5
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Product Categories: pharmacetical;chiral;Chiral Reagent;Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Esters (Chiral);Synthetic Organic Chemistry;Heterocyclic Building Blocks;Chiral Reagents;Heterocycles;Intermediates
• Mol File: 52373-72-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 70-75 °C10 mm Hg(lit.)
• Flash Point: 173 °F
• Appearance: /
• Density: 1.106 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.404mmHg at 25°C
• Refractive Index: n20/D 1.426
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
• BRN: 4292353
• CAS DataBase Reference: (R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER(52373-72-5)
• EPA Substance Registry System: (R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER(52373-72-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 52373-72-5(Hazardous Substances Data)

Usage

Description

(R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER, also known as Methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate, is a dioxolane derivative with a molecular structure that features a methyl ester group. It is characterized by its chiral center, which gives it unique properties and potential applications in various fields.

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

• 18289-89-9 methyl (2R)-2,3-dihydroxypropanoate 
• 116-11-0 2-Methoxypropene 
• 67-56-1 methanol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 186581-53-3 diazomethane 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 615-34-9 methyl glycerate 
• 77-76-9 2,2-dimethoxy-propane 
• 135547-99-8 Calcium (4R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 74-88-4 methyl iodide 

Downstream Products

• 85364-10-9 2-chloro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 55032-17-2 (4R)-4-benzyloxycarbonyl-2,2-dimethyl-1,3-dioxolane 
• 171775-72-7 (R)-N-benzyl 2,2-dimethyl-1,3-dioxolane-4-carboxamide 
• 18289-89-9 methyl (2R)-2,3-dihydroxypropanoate 
• 1379764-50-7 (S,E)-benzyl 2-(dibenzylamino)-7-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxohept-5-enoate 
• 885693-41-4 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(R)-(+)-(2,2-dimethyl[1,3]dioxolane-4-carbonyl)piperidin-4-yl]phenyl}amide 
• 82268-15-3 2-<(R)-2,2-dimethyl-1,3-dioxolane-4-yl>-2-propanol 
• 201420-74-8 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 170164-82-6 (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylpropan-1-one 
• 16354-97-5 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone 
• 143159-97-1 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 874384-08-4 benzyl (2S)-2-(dibenzylamino)-8-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-8-oxo-6-octenoate 

Relevant articles and documents

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.

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

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.