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

Uses

Different sources of media describe the Uses of 52373-72-5 differently. You can refer to the following data:
1. (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxylic Acid Methyl Ester is a dioxolane derivative used in the preparation of matrix metalloproteinases (MMP) inhibitors.
2. Methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate may be used as a starting material to synthesize (2R)-[1-2H2]-glycerol, a probe to study the stereochemistry of glycerol metabolism in Streptomyces cattleya. It may also be used to synthesize organic building blocks like (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.

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 
• 116-11-0 2-Methoxypropene 
• 67-64-1 acetone 
• 1067-52-3 tributyltin methoxide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 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 
• 77-76-9 2,2-dimethoxy-propane 
• 615-34-9 methyl glycerate 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 61821-86-1 (R)-2,2-dimethyl-1,3-dioxolan-4-yl methyl ketone 
• 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 
• 288162-71-0 (R)-2-Benzyloxymethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 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 
• 171775-72-7 (R)-N-benzyl 2,2-dimethyl-1,3-dioxolane-4-carboxamide 
• 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 
• 55032-17-2 (4R)-4-benzyloxycarbonyl-2,2-dimethyl-1,3-dioxolane 

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.