95422-24-5

Usage

Uses

Used in Perfumery and Fragrance Industry:
METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE is used as a flavor and fragrance agent for its distinctive fruity apple-like scent, adding a pleasant aroma to perfumes and scented products.
Used in Chemical Industrial Applications:
Due to its stability, low reactivity, and non-toxicity, METHYL (4S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETATE is utilized in various chemical industrial processes where its properties contribute to the effectiveness and safety of the products being developed.

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

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

Downstream Products

• 185996-33-2 (S)-4-(2,2-dimethyl)-1,3-dioxolane acetamide 
• 274933-34-5 2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-oxazole-4-carboxylic acid methyl ester 
• 127929-56-0 (E)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oct-3-en-2-one 
• 127929-55-9 (E)-4-Cyclohexyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-2-one 
• 127929-60-6 (E)-(S)-4-Cyclohexyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-2-ol 
• 127929-59-3 (E)-(R)-4-Cyclohexyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-2-ol 
• 110594-72-4 2-Benzyloxycarbonylamino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-butyric acid 
• 110594-76-8 benzyl (2SR,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 
• 110594-80-4 benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate 
• 82780-39-0 (S)-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane 
• 139884-77-8 (S)-2,2-Dimethyl-4-(2-trityloxy-ethyl)-[1,3]dioxolane 
• 61448-27-9 (R)-(-)-phoracantholide I 
• 138253-37-9 1-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 138253-43-7 (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide 

Relevant academic research and scientific papers

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.

Toward an Asymmetric Synthesis of Bistramide K

The bistramides family has shown antitumoral activity. More specifically bistramide K exhibits lower toxicity than its congeners. In this work, we describe a highly stereoselective and convergent synthesis of two building blocks of the marine metabolite b

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.

Studies directed towards the total synthesis of koshikalide: Stereoselective synthesis of the macrocyclic core

The stereoselective synthesis of the macrolactone core of the natural product koshikalide is described. Starting with readily available 1,4-butanediol and malic acid as synthons, our synthetic strategy involved the reiterative application of Gilman's reaction, Swern oxidation and Sharpless asymmetric epoxidation to establish the required stereocentres. Other key steps in the synthesis include Negishi cross coupling and Horner-Wadsworth-Emmons (HWE) reactions for construction of the main fragments. The 14-membered lactone ring was prepared by a selective Mitsunobu macrolactonization approach.

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

Stereoselective synthesis of tetrahydropyranyl diarylheptanoids (-)-centrolobine and (+)-centrolobine

A versatile chiron approach to the tetrahydropyranyl diarylheptanoid natural products (-)-centrolobine and (+)-centrolobine has been described. The use of an aldol reaction followed by reductive etherification for the formation of tetrahydropyran ring is of importance. Georg Thieme Verlag Stuttgart · New York.

Structure elucidation and stereoselective total synthesis of pavettamine, the causal agent of gousiekte

The structure elucidation of a novel natural product pavettamine (1), the causal agent of the plant toxicosis gousiekte, is reported. The structure was defined by analysis of NMR and MS data and the relative configuration followed from the 13C NMR data of the acetonide derivative. The absolute stereochemistry was established by total synthesis from (2S)-malic acid using chiral sulfoxide methodology as (2S,4R,8R,10S)-1,11-diamino-6-aza-undecane-2,4,8,10-tetraol.

Application of stereoselective ether transfer to the synthesis of isotactic polyethers

An efficient, convergent synthetic strategy has been developed which enables the synthesis of a series of naturally occurring isotactic polymethoxy compounds. Ether transfer followed by a hydride workup enables simultaneous, diastereoselective production of two methoxy centers in a single step. High yields and diastereoselectivity are observed even in stereochemically rich, polyoxygenated systems. Direct generation of bis-methyl ether moieties from methoxymethyl ethers minimizes the need for typical protective group strategies and the use of expensive methyl transfer reagents. Moreover, the simultaneous generation of a terminal primary iodide serves as a coupling partner for the generation of higher order congeners.

Highly stereoselective hydrogenations-as key-steps in the total synthesis of statins

Statins are inhibitors of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase (HMG-CoA reductase) and became the standard of care for treatment of hypercholesterolemia because of their efficacy, safety, and long-term benefits. They are administered as diaste

Synthesis and highly stereoselective hydrogenation of the statin precursor ethyl (5S)-5,6-isopropylidenedioxy-3-oxohexanoate

A search for the large-scale preparation of (5S)-5,6-(isopropylidenedioxy)- 3-oxohexanoates (2) - a key intermediate in the synthesis of pharmacologially important statins - starting from (S)-malic acid is described. The synthesis of the required initial compound methyl (3S)-3,4-(isopropylidenedioxy)butanoate (1) by Moriwake's reduction of dimethyl (S)-malate (3) has been improved. Direct 2-C chain elongation of ester 1 using the lithium enolate of tert-butyl acetate has been shown to be successful at a 3- to 5-fold excess of the enolate. Unfortunately, the product, tert-butyl (5S)-5,6-(isopropylidenedioxy)-3- oxohexanoate (2a) is unstable during distillation. Ethyl (5S)-5,6- (isopropylidenedioxy)-3-oxohexanoate (2b) was prepared alternatively on a multigram scale from (3S)-3,4-(isopropylidenedioxy)butanoic acid (7) by activation with N,N′-carbonyldiimidazole and subsequent reaction with Mg(OOCCH2COOEt)2. A convenient pathway for the in situ preparation of the latter is also described. Ethyl ester (2b) can be advantageously purified by distillation. The stereochemistry of the catalytic hydrogenation of β-keto ester (2b) to ethyl (55)-5,6-(isopropylidenedioxy)- 3-hydrohyhexanoate (syn-6 and anti-6) has been studied using a number of homogeneous achiral and chiral Rh(I) and Ru(II) complexes with phosphine ligands. A comparison of Rh(I) and Ru(II) catalysts with (S)- and (R)-BINAP as chiral ligands revealed opposite activity in dependence on the polarity of the solvent. No influence of the chiral backbone of substrate 2b on the enantioselectivity was noted. A ratio of syn-6/anti-6 = 2.3 was observed with an achiral (Ph3P)3RuCl2 catalyst. Ru[(R)-Tol-BINAP]Cl2 neutralized with one equivalent of AcONa afforded the most efficient catalytic system for the production of optically pure syn-(5S)-5,6-isopropylidenedioxy-3-hydroxyhexanoate (syn-6) at a preparative substrate/catalyst ratio of 1000:1.