95422-24-5

Basic information

• Product Name: METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE
• Synonyms: (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETIC ACID METHYL ESTER;methyl(4s)-(+)-2,2-dimethyl-1,3-dioxolane-4-acet;METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE;METHYL-(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE;1,3-DIOXOLANE-4-ACETIC ACID, 2,2-DIMETHYL-, METHYL ESTER, (S);AIDS-131617;METHYL (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)ACETATE
• CAS NO: 95422-24-5
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 95422-24-5.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 192-194 °C(lit.)
• Flash Point: 149 °F
• Appearance: /
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: n20/D 1.615(lit.)
• CAS DataBase Reference: METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE(95422-24-5)
• EPA Substance Registry System: METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE(95422-24-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 95422-24-5(Hazardous Substances Data)

Usage

General Description

Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate is a specific organic compound that falls into the category of flavour and fragrance agents. It possesses a strong aroma and is often used in perfumes and scented products for its fruity apple-like scent. Structurally, this compound is classified as a cyclic acetal and has a chiral center, meaning it has the capability to exist in two enantiomeric forms. As suggested by its name, this particular version is the (4S)-(+)-enantiomer. The compound's chemical features include stability, low reactivity and non-toxicity, which make it popular in the chemical industrial applications.

InChI:InChI=1/C8H14O4/c1-8(2)11-5-6(12-8)4-7(9)10-3/h6H,4-5H2,1-3H3/t6-/m0/s1

Upstream product

• 66178-02-7 malic acid monomethyl ester 
• 67-64-1 acetone 
• 90414-36-1 methyl (3S)-3,4-dihydroxybutyrate 
• 77-76-9 2,2-dimethoxy-propane 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 617-55-0 dimethyl (S)-malate 
• 116-11-0 2-Methoxypropene 
• 216861-20-0 (3S)-3,4-dihydroxybutanoate 
• 67-56-1 methanol 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 87319-12-8 (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 541513-63-7 (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester 
• 541513-52-4 (4R)-4-benzyl-3-{(2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyryl}oxazolidin-2-one 
• 185996-39-8 4-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazole 
• 185996-38-7 4-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4,5-dihydro-thiazol-4-ol 
• 114884-40-1 (S)-3,4-O-isopropylidene-3,4-dihydroxybutyltriphenylphosphonium iodide 
• 139884-77-8 (S)-2,2-Dimethyl-4-(2-trityloxy-ethyl)-[1,3]dioxolane 
• 82780-39-0 (S)-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane 
• 110594-80-4 benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate 
• 110594-76-8 benzyl (2SR,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 
• 110594-72-4 2-Benzyloxycarbonylamino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-butyric acid 
• 127929-59-3 (E)-(R)-4-Cyclohexyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-2-ol 
• 127929-60-6 (E)-(S)-4-Cyclohexyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-2-ol 

Relevant articles and documents

Glycosyl-nucleolipids as new bioinspired amphiphiles

Four new Glycosyl-NucleoLipid (GNL) analogs featuring either a single fluorocarbon or double hydrocarbon chains were synthesized in good yields from azido thymidine as starting material. Physicochemical studies (surface tension measurements, differential scanning calorimetry) indicate that hydroxybutanamide-based GNLs feature endothermic phase transition temperatures like the previously reported double chain glycerol-based GNLs. The second generation of GNFs featuring a free nucleobase reported here presents a better surface activity (lowerγlim) compared to the first generation of GNFs.

The total synthesis of calcium atorvastatin

A practical and convergent asymmetric route to calcium atorvastatin (1) is reported. The synthesis of calcium atorvastatin (1) was performed using the remote 1,5-anti asymmetric induction in the boron-mediated aldol reaction of β-alkoxy methylketone (4) with pyrrolic aldehyde (3) as a key step. Calcium atorvastatin was obtained from aldehyde (3) after 6 steps, with a 41% overall yield.

Total synthesis of (-)-zampanolide and structure-activity relationship studies on (-)-dactylolide derivatives

A new total synthesis of the marine macrolide (-)-zampanolide (1) and the structurally and stereochemically related non-natural levorotatory enantiomer of (+)-dactylolide (2), that is, ent-2, has been developed. The synthesis features a high-yielding, selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction to close the 20-membered macrolactone ring of 1 and ent-2. The β-keto phosphonate/aldehyde precursor for the ring-closure reaction was obtained by esterification of a ω-diethylphosphono carboxylic acid fragment and a secondary alcohol fragment incorporating the THP ring that is embedded in the macrocyclic core structure of 1 and ent-2. THP ring formation was accomplished through a segment coupling Prins-type cyclization. Employing the same overall strategy, 13-desmethylene-ent-2 as well as the monocyclic desTHP derivatives of 1 and ent-2 were prepared. Synthetic 1 inhibited human cancer cell growth in vitro with nM IC50 values, while ent-2, which lacks the diene-containing hemiaminal-linked side chain of 1, is 25- to 260-fold less active. 13-Desmethylene-ent-2 as well as the reduced versions of ent-2 and 13-desmethylene-ent-2 all showed similar cellular activity as ent-2 itself. The same activity level was attained by the monocyclic desTHP derivative of 1. Oxidation of the aldehyde functionality of ent-2 gave a carboxylic acid that was converted into the corresponding N-hexyl amide. The latter showed only μM antiproliferative activity, thus being several hundred-fold less potent than 1. It's the side chain that matters: The marine macrolide (-)-zampanolide (1) has been synthesized via (-)-dactylolide (ent-2), the non-natural enantiomer of the marine natural product (+)-dactylolide (2), employing a high-yielding intramolecular Horner-Wadsworth-Emmons reaction to close the macrolactone ring. While the hemiaminal-linked side chain in 1 is crucial for nanomolar antiproliferative activity, the methylene group and the aldehyde functionality in ent-2 are dispensable. A monocyclic destetrahydropyran derivative of 1 shows equal activity as ent-2. Copyright