82954-65-2

Usage

Uses

Used in Organic Synthesis:
(S)-(+)-(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE is used as a resolving agent for chiral acids, facilitating the separation of enantiomers which is vital for the creation of pure compounds with specific biological activities.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, (S)-(+)-(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE is used as a catalyst in various chemical reactions, contributing to the development of new drugs and bioactive compounds. Its ability to influence the stereochemistry of reactions is particularly valuable in synthesizing enantiomerically pure pharmaceuticals.
Used in Agrochemicals:
(S)-(+)-(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE also finds application in the agrochemical sector, where it serves as a catalyst or resolving agent in the synthesis of enantiomerically pure pesticides and other agrochemicals, ensuring the desired biological activity and reducing potential environmental impact.
Used in the Production of Enantiopure Compounds:
Due to its chiral nature, (S)-(+)-(2,2-DIMETHYL-[1,3]-DIOXOLAN-4-YL)-METHYLAMINE is essential in the production of enantiopure compounds, which have significant applications across various fields, including medicine where the different enantiomers of a drug can have vastly different effects.

Upstream product

• 117465-48-2 (S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 
• 40137-25-5 1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] 
• 23735-39-9 (R)-4-(iodomethyl)-2,2-dimethyl-1,3-dioxolane 
• 83461-40-9 methanesulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 
• 77-76-9 2,2-dimethoxy-propane 
• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 109208-40-4 N-benzyl-N-amine 
• 185996-33-2 (S)-4-(2,2-dimethyl)-1,3-dioxolane acetamide 
• 85820-82-2 (S)-1-azido-1-deoxy-2,3-O-isopropylidene-glycerol 

Downstream Products

• 134038-71-4 (S)-4-benzyloxycarbonylaminomethyl-2,2-dimethyl-1,3-dioxolane 
• 61278-21-5 (S)-3-Amino-1,2-propanediol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 14437-88-8 (2R)-3-bromo-1,2-propanediol 
• 1161881-58-8 (2Z)-1-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime 
• 1161881-57-7 (2E)-1-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-3-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}propanone O-benzyloxime 
• 851303-51-0 C₁₈H₂₆N₂O₅ 

Relevant academic research and scientific papers

Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.

Stereochemistry-Controlled Supramolecular Architectures of New Tetrahydroxy-Functionalised Amphiphilic Carbocyanine Dyes

The syntheses of novel amphiphilic 5,5′,6,6′-tetrachlorobenzimidacarbocyanine (TBC) dye derivatives with aminopropanediol head groups, which only differ in stereochemistry (chiral enantiomers, meso form and conformer), are reported. For the achiral meso form, a new synthetic route towards asymmetric cyanine dyes was established. All compounds form J aggregates in water, the optical properties of which were characterised by means of spectroscopic methods. The supramolecular structure of the aggregates is investigated by means of cryo-transmission electron microscopy, cryo-electron tomography and AFM, revealing extended sheet-like aggregates for chiral enantiomers and nanotubes for the mesomer, respectively, whereas the conformer forms predominately needle-like crystals. The experiments demonstrate that the aggregation behaviour of compounds can be controlled solely by head group stereochemistry, which in the case of enantiomers enables the formation of extended hydrogen-bond chains by the hydroxyl functionalities. In case of the achiral meso form, however, such chains turned out to be sterically excluded.

Synthesis of phosphonoglycine backbone units for the development of phosphono peptide nucleic acids

A series of phosphono-modified backbone mimics based on achiral and chiral N-(dihydroxypropyl)glycine units were obtained by sequential addition of phosphonate and nucleobase moieties to suitably protected dihydroxypropylamines. Simple synthetic strategies enabled the preparation of various target derivatives that will be useful as building blocks for the preparation of new synthetic polymers containing a phosphonate internucleotide linkage in place of the standard phosphodiester bond. Copyright

Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics

Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave Ki values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-d-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4- methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(±)-65 vs (±)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts.

ACYCLIC AMINE INHIBITORS OF 5'-METHYLTHIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE

The present invention relates to compounds of the general formula (I) which are inhibitors of 5'-methylthioadenosine phosphorylase or 5'-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5'-methylthioadenosine phosphorylase or 5'-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds.

PROCESS FOR THE PREPARATION OF PROTECTED DIHYDROXYPROPYL TRIALKYLAMMONIUM SALTS AND DERIVATIVES THEREOF

A process for the preparation of protected dihydroxypropyl trialkylammonium salts, particularly in chiral form is described. In particular, a process for the preparation of (2,2-dimethyl-1,3-dioxolan-4-ylmethyl)trialkylammonium salts, particularly in chiral form is described. Furthermore, a process is described wherein the (2,2-dimethyl-1,3-dioxolan-4ylmethyl)trialkylammonium salts is a 2,2-dimethyl-1,3-dioxolan-4-ylmethyl trimethylammonium salt, preferably in chiral form. The protected dihydroxypropyl trialkylammonium salts lead to L-carnitine (9) when in chiral form (5).

COMPOUNDS AND METHODS FOR TREATING TOLL-LIKE RECEPTOR 2-RELATED DISEASES AND CONDITIONS

The present invention relates to compounds and methods useful in the prevention or treatment of diseases or conditions associated with Toll-like receptor 2 activation.

Synthesis of glycidol- and sugar-derived bicyclic β- and γ/δ-amino acids for peptidomimetic design

Constrained bicyclic β- and γ/δ-amino acids using glycidol and sugar derivatives were developed. The synthetic strategies involved epoxide ring opening of a glycidol derivative, and subsequent coupling with sugar-derived amines, leading to di- or trisubst

PROCESS FOR THE PREPARATION OF PROTECTED 3-AMINO-1,2-DIHYDROXYPROPANE ACETAL AND DERIVATIVES THEREOF

A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.

Process for the preparation of protected 3-amino-1,2-dihydroxypropane acetal and derivatives thereof

A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.