23735-43-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate is used as a key reactant for the synthesis of various pharmaceutical compounds, such as travoprost (T715600), a potent topical ocular agent with significant activity in treating glaucoma and ocular hypertension. Its unique structure allows for the development of analogs with improved efficacy and reduced side effects.
Additionally, (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate is used as a starting material for the preparation of p38 mitogen-activated protein (MAP) kinase inhibitors. These inhibitors play a crucial role in the development of treatments for various inflammatory diseases, autoimmune disorders, and certain types of cancer, as they target the p38 MAP kinase pathway, which is involved in cellular responses to stress and inflammation.

InChI:InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/m0/s1

Upstream product

• 70987-78-9 (S)-Glycidyl tosylate 
• 67-64-1 acetone 
• 4306-35-8 1,2-isopropylidene-D-glucitol 
• 141656-30-6 (R)-(+)-3-tosyloxypropane-1,2-diol dipropionate 
• 141656-36-2 Propionic acid (S)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester 
• 51704-66-6 (+/-)-2,3-dihydroxypropyl tosylate 
• 119970-97-7 (+)-5-O-(p-Toluolsulfonyl)-D-ribonsaeure-γ-lacton 
• 40519-00-4 2,3-O-Isopropylidene-5-O-(p-tolylsulfonyl)-D-ribono-1,4-lactone 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 50765-70-3 (S)-1-tosyloxy-2,3-propanediol 

Downstream Products

• 1044590-54-6 [5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]{3-[(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}ketone 
• 1155773-19-5 C₃₁H₄₁N₃O₅ 
• 1155773-20-8 C₃₁H₄₁N₃O₅ 
• 865239-03-8 4-{1-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol 
• 91575-89-2 Toluene-4-sulfonic acid (S)-2,3-bis-(tert-butyl-diphenyl-silanyloxy)-propyl ester 
• 168427-92-7 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 499136-63-9 (4R)-2,2-dimethyl-4-(15-phenyl-2,5,8,11,14-pentaoxapentadecyl)-1,3-dioxolane 
• 143393-27-5 (2S,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-[{(4-aminophenyl)thio}methyl]-1,3-dioxolane 
• 872202-40-9 (R)-1-O-(2-chloro-3-pyridinyl)-2,3-O-isopropylideneglycerol 

Relevant academic research and scientific papers

Mycolic Acids Constitute a Scaffold for Mycobacterial Lipid Antigens Stimulating CD1-Restricted T Cells

CD1-restricted lipid-specific T lymphocytes are primed during infection with Mycobacterium tuberculosis, the causative agent of tuberculosis. Here we describe the antigenicity of glycerol monomycolate (GroMM), which stimulates CD1b-restricted CD4+/s

Gold(I)-catalyzed, one-pot, oxidative formation of 2,4-disubstituted thiazoles: Application to the synthesis of a pateamine-related macrodiolide

Thiazoles are important heterocyclic motifs in many target molecules. Extension of a reported gold(I)-catalyzed oxidative coupling of alkynes and thioamides to the synthesis of functionalized thiazole-containing products is presented, including the compatibility of this reaction with ester, protected hydroxyl, alkene and thioether groups. The utility of this one-pot process is demonstrated in the preparation of the thiazole-containing macrodiolide of a simplified analogue of pateamine A.

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.

Discovery of novel potent HCV NS5B polymerase non-nucleoside inhibitors bearing a fused benzofuran scaffold

This letter describes the discovery of a fused benzofuran scaffold viable for preparing a series of novel potent HCV NS5B polymerase non-nucleoside inhibitors. Designed on the basis of the functionalized benzofuran derivative nesbuvir (HCV-796), these com

SMALL MOLECULE INHIBITORS OF FIBROSIS

Described herein are compounds and compositions for the treatment of a fibrotic disease.

Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic

Itraconazole (ITZ) is an FDA-approved member of the triazole class of antifungal agents. Two recent drug repurposing screens identified ITZ as a promising anticancer chemotherapeutic that inhibits both the angiogenesis and hedgehog (Hh) signaling pathways. We have synthesized and evaluated first- and second-generation ITZ analogues for their anti-Hh and antiangiogenic activities to probe more fully the structural requirements for these anticancer properties. Our overall results suggest that the triazole functionality is required for ITZ-mediated inhibition of angiogenesis but that it is not essential for inhibition of Hh signaling. The synthesis and evaluation of stereochemically defined des-triazole ITZ analogues also provides key information as to the optimal configuration around the dioxolane ring of the ITZ scaffold. Finally, the results from our studies suggest that two distinct cellular mechanisms of action govern the anticancer properties of the ITZ scaffold.

PROCESS FOR PREPARATION OF PROSTAGLANDIN F2 ALPHA ANALOGUES

A convergent synthesis of the prostaglandin F2α analogues, travoprost and bimatoprost, was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone with an enantiomerically pure aldehyde ω-chain synthon. The novel convergent strategy allows the synthesis of a whole series of prostaglandin analogues of high purity from a common and structurally advanced prostaglandin intermediate.

PROCESS FOR PREPARATION OF PROSTAGLANDIN F2α ANALOGUES

A convergent synthesis of the prostaglandin F2α analogues, travoprost and bimatoprost, was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone with an enantiomerically pure aldehyde ω-chain synthon. The novel convergent strategy allows the synthesis of a whole series of prostaglandin analogues of high purity from a common and structurally advanced prostaglandin intermediate.

A novel convergent synthesis of the potent antiglaucoma agent travoprost

The 16-(3-trifluoromethyl)phenoxy PGF2α analogue travoprost (8a) has potent topical ocular activity. A novel convergent synthesis of 13,14-en-15-ol PGF2α analogues was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone (5Z)-(+)-15 with a new enantiomerically pure aldehyde ω-chain synthon (S)-(-)-16a. Subsequent hydrolysis of protecting groups and final esterification of fluprostenol (7a) yielded travoprost (8a). The main advantages are the preparation of high purity travoprost (8a) and the application of comparatively cheap reagents. The novel convergent strategy allows the synthesis of a whole series of 13,14-en-15-ol PGF2α analogues from a common and structurally advanced prostaglandin intermediate 15. The preparation and identification of two synthetic impurities, 15-epi isomer (8b) of travoprost and a new prostaglandin related ester (5Z)-(+)-18, are also described.

Asymmetric synthesis and effect of absolute stereochemistry of YCZ-2013, a brassinosteroid biosynthesis inhibitor

The four stereoisomers of 2RS,4RS-1-[[2-(2,4-dichlorophenyl)-4-(2-(2- propenyloxy)phenoxymethyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole (YCZ-2013), a novel brassinosteroid biosynthesis inhibitor, were prepared. The diastereomers of 2RS,4R-5 and 2RS,4S-5 were prepared by using the corresponding optically pure R and S toluene-4-sulfonic acid 2,3-dihydroxypropyl ester (R-4,S-4). The enatiomerically and diastereomerically pure acetonide (5) was obtained by a method involving diastereoselective crystallisation of the tosylate salt, followed by re-equilibration with the mother liquor and chromatography. The optical purity of four target compounds (YCZ-2013) was confirmed by chiral high-performance liquid chromatography (HPLC) and NMR. The effects of these stereoisomers on Arabidopsis stem elongation indicated that the cis isomers of 2S,4R-YCZ-2013 and 2R,4S-YCZ-2013 exhibited potent inhibitory activity with IC50 values of approximately 24 ± 3 and 24 ± 2 nM, respectively. The IC50 values of the trans isomers of 2S,4S-YCZ-2013 and 2R,4R-YCZ-2013 are approximately 1510 ± 50 and 3900 ± 332 nM, respectively. Co-application of brassinolide (10 nM), the most potent BR, and GA3 (1 μM) to Arabidopsis seedlings grown in the dark with 2R,4S-YCZ-2013 and 2S,4R-YCZ-2013 revealed that brassinolide recovered the induced dwarfism of Arabidopsis seedlings, whereas GA3 showed no effect.