73346-73-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate is used as a building block in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of diverse drug molecules with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate serves as a key intermediate in the production of various agrochemicals, contributing to the development of effective pest control agents and other agricultural products.
Used in Antioxidant Applications:
(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate is studied for its potential antioxidant properties, which could be utilized in the development of health supplements or pharmaceuticals aimed at reducing oxidative stress and promoting overall health.
Used in Anti-inflammatory Applications:
(4S,5S)-diethyl 2,2-diMethyl-1,3-dioxolane-4,5-dicarboxylate's anti-inflammatory properties make it a candidate for use in the development of treatments for various inflammatory conditions, potentially offering new therapeutic options for patients suffering from such ailments.

Upstream product

• 13811-71-7 diethyl (2S,3S)-tartrate 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 108-21-4 Isopropyl acetate 

Downstream Products

• 5754-27-8 (4S,5S)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde 
• 51064-65-4 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol 
• 117780-06-0 [(4S,5S)-5-(Hydroxy-di-o-tolyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-di-o-tolyl-methanol 
• 137365-16-3 (4S,5S)-2,2-dimethyl-trans-4,5-bis(di(2-naphthyl)hydroxymethyl)-1,3-dioxolane 

Relevant academic research and scientific papers

Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C[sbnd]H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C[sbnd]H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described.

Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents

A series of 2,8-diazaspiro[4.5]decan-1-one derivatives were designed, synthesized and screened for their inhibition activities against chitin synthase (CHS) and antimicrobial activities in vitro. The biological assays revealed that compounds 4a, 4e, 4h, 4j, 4o, 4q and 4r exhibited moderated to excellent potency against CHS with IC50 values ranging from 0.12 to 0.29 mM. Compounds 4e, 4j with IC50 value of 0.13 mM, 0.12 mM respectively, showed excellent inhibition potency among these compounds, which were similar to that of polyoxin B whose IC50 value was 0.08 mM. Meanwhile, the screening of the antifungal activity showed that compounds 4j and 4r had the same potency of inhibiting the growth of A. fumigatus with MIC value of 0.08 mmol/L. Compound 4d displayed excellent activity against C. albicans (ATCC 90023) with MIC value of 0.04 mmol/L, which was superior to fluconazole (0.104 mmol/L) and polyoxin B (0.129 mmol/L). The result of antibacterial assay showed that these compounds had little potency against those selected bacteria strains including three Gram-positive bacteria and three Gram-negative bacteria. Furthermore, the combination use of 4c-fluconazole, 4i-fluconazole, 4j-fluconazole, and 4o-fluconazole against C. albicans,A. fumigatus and A. flavus showed additive or synergistic effects. These results indicated that the designed compounds serve as potential chitin synthase inhibitors and have selectively antifungal activities.

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The compounds of Formula I, Formula Ia, and Formula Ib are described herein along with their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds inhibit PRMT5 and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, Parkinson's disease and the like.

Supramolecular gels from sugar-linked triazole amphiphiles for drug entrapment and release for topical application

A simple molecular framework obtained by cross-linking a hydrophobic chain with S,S- and R,R-tetritol by the copper-catalysed azide-alkyne cycloaddition reaction is found to serve as an excellent bioisostere for self-assembly. The hexadecyl-linked triazolyl tetritol composite spontaneously self-assembles in n-hepane and methanol to form hierarchical organogels. Microscopic analyses and X-ray diffraction studies demonstrate eventual formation of nanotubes through lamellar assembly of the amphiphiles. A rheological investigation shows solvent-dictated mechanical properties that obey power law behavior similar to other low molecular weight gelators (LMOGs). The gel network was then utilized for the entrapment of drugs e.g. ibuprofen and 5-fluorouracil, with tunable mechanical behaviour under applied stress. The differential release profiles of the drugs over a period of a few hours as a result of the relative spatio-temporal location in the supramolecular network can be utilized for topical formulations.

Preparation method of chiral catalyst ligand TADDOLs in asymmetric synthesis

The invention discloses a preparation method of a chiral catalyst ligand TADDOLs in asymmetric synthesis. The preparation method comprises the following steps of using chiral diethyl tartrate as raw material, and reacting with 2,2-dimethoxypropane and triethyl orthoformate, so as to obtain O,O-isopropylidene diethyl tartrate; enabling brominated aromatic hydrocarbon and isopropyl magnesium bromideto react in a solvent; finally, adding the O,O-isopropylidene diethyl tartrate, so as to obtain a target product, namely the chiral catalyst ligand TADDOLs. The preparation method has the advantagesthat the raw materials are bulk chemicals, the industrial cost is low, the reaction process is moderate and controllable, the post-treatment is concise and efficient, the difficulty in industrial production of the series of compound is decreased, and the cost is reduced; the chiral catalyst ligand TADDOLs has been widely applied into the asymmetric chiral synthesis; especially, when the chiral catalyst ligand TADDOLs and metal form a complex as the catalyst in the chiral oriented synthesis, the effect is obvious; the catalyzing effect is excellent, the process of chiral detachment of despinner compound is reduced, and the synthesis cost of chiral medicine is reduced.

Stereoselective synthesis of the lichen metabolite, (+) montagnetol and its congeners as antimicrobial agents

In view of structural diversity, (+) montagnetol, the major metabolite of the fruticose lichen, Roccella montagnei was synthesized along with three of its congeners by employing highly efficient protocols. (+) Montagnetol (2 R, 3S; 11) and (-) montagnetol (2S, 3R; 5) were synthesized in 7 and 9 steps, respectively, from L-ascorbic acid. The two new congeners 3 (2 R, 3R) and 6 (2S, 3S), which differ in configuration at C-2 and C-3 positions of the (+) montagnetol, were synthesized from (?) diethyl D-tartrate and (+) diethyl L-tartrate, respectively. The synthesized compounds were evaluated in vitro for antimicrobial activity against two Gram-positive (S. aureus and E. coli) and two Gram-negative (S. typhi and P. aeruginosa) bacteria and one fungal strain Candida albicans. Interestingly, the congener 3 showed promising anti-bacterial activity (MIC: 0.062 μg/ml) against P. aeruginosa, whereas the congener 6 displayed potent anti-fungal activity (MIC: 0.062 μg/ml) against C. Albicans.

Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization

A highly attractive route toward macrolactones, which form the cyclic scaffold of a multitude of diverse natural compounds, is described. Although many chemical approaches to this structural motif have been explored, an asymmetric variant of the cyclization is unprecedented. Herein we present an enantioselective macrolactonization through an intramolecular atom-economical rhodium-catalyzed coupling of ω-allenyl-substituted carboxylic acids. The use of a modified diop ligand, chiral DTBM-diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β-unsaturated carboxylic acids and depsipeptides, and provided the desired macrocycles with very high enantio- and diastereoselectivity.

A convergent approach for the total synthesis of the α-glucosidase inhibitor (-)-panaxjapyne-C

The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers l-(+)-diethyltartrate and d-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps.

Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization

The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5- methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one.

Total synthesis of the marine toxin phorboxazole A using palladium(ii)-mediated intramolecular alkoxycarbonylation for tetrahydropyran synthesis

The potent antitumor agent phorboxazole A was synthesized from six subunits comprising C1-C2 (115), C3-C8 (98), C9-C19 (74), C20-C32 (52), C33-C41 (84) and C42-C46 (85). Tetrahydropyrans B and C containing cis-2,6-disubstitution were fabricated via palladium(ii)-mediated intramolecular alkoxycarbonylation which, in the case of tetrahydropyran C, was carried out with catalytic palladium(ii) and p-benzoquinone as the stoichiometric re-oxidant. Tetrahydropyran D was obtained by a stereoselective tin(iv)-catalyzed coupling of a C9 aldehyde with an allylsilane, and the C19-C20 connection was made using a completely stereoselective Wittig-Schlosser (E) olefination. Coupling of the oxazole C32 methyl substituent with the intact C33-C46 δ-lactone 3 was accompanied by elimination of the vinyl bromide to a terminal alkyne, but the C32-C33 linkage was implemented successfully with 83 and C33-C41 lactone 84. The C42-C46 segment of the side chain was then appended via Julia-Kocienski olefination. The macrolide portion of phorboxazole A was completed by means of an Ando-Still-Gennari intramolecular (Z)-selective olefination at C2-C3 which required placement of a (dimethoxyphosphinyl)acetate moiety at C24. Final deprotection led to phorboxazole A via a route in which the longest linear sequence is 37 steps and the overall yield is 0.36%.