23788-74-1

Basic information

• Product Name: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
• Synonyms: p-Toluenesulfonic acid [(R)-2,2-dimethyl-1,3-dioxolane-4β-yl]methyl ester;p-Toluenesulfonic acid [R,(-)]-2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester;p-Toluenesulfonic acid [R,(-)]-2,2-dimethyl-1,3-dioxolane-4-ylmethyl ester;(R)-(-)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate,97%;D-α,β-Isopropylideneglycerol-γ-tosylate;p-Toluenesulfonic acid ((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester;Toluene-4-sulfonic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)methyl ester;(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate >=99.0% (sum of enantiomers, GC)
• CAS NO: 23788-74-1
• Molecular Formula: C₁₃H₁₈O₅S
• Molecular Weight: 286.34
• Product Categories: chiral;Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 23788-74-1.mol
• Article Data: 46

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 398.71°C (rough estimate)
• Flash Point: >230 °F
• Appearance: clear yellow to light brown viscous liquid
• Density: 1.208 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.506(lit.)
• Storage Temp.: −20°C
• Solubility: Dichloromethane; Chloroform; Ethyl Acetate; Methanol; DMF
• BRN: 89800
• CAS DataBase Reference: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE(23788-74-1)
• EPA Substance Registry System: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE(23788-74-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 23788-74-1(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to light brown viscous liquid

Uses

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate is a chiral building block. It is used to prepare the antifungal agent ketoconazole. It is also used to prepare acyclic Nucleotide Analogs Derived from 8-Azapurines with antiviral activities.

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-/m1/s1

Upstream product

• 70987-78-9 (S)-Glycidyl tosylate 
• 67-64-1 acetone 
• 20196-71-8 (2S)-2,3-bis(benzyloxy)propanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 102418-34-8 1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 

Downstream Products

• 116156-85-5 (R)-(+)-2,3-O-isopropylideneglycerol-1-diphenylphosphane 
• 215302-21-9 N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 215302-17-3 N-[(2S,3R,4R,5S,6R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-hydroxymethyl-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 215302-25-3 N-[(2S,3R,4R,5S,6R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 872202-37-4 (S)-1-O-(2-chloro-3-pyridinyl)-2,3-O-isopropylideneglycerol 
• 104392-60-1 (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate 
• 259206-83-2 1,3-bis[(R,R)-2,3-O-isopropylideneglycerol-1-phenylphosphono]propane 
• 168427-93-8 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 163759-88-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 4549-72-8 sodium o-cresolate 
• 348640-39-1 2-[5-({S}-(+)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 1255305-44-2 {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)pyridin-2-yl]methanone 

Relevant articles and documents

Comparative studies with the enantiomers of the glycol metabolite of propranolol and their effects on the cardiac β-adrenoceptor

-

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.

Synthesis and antimicrobial screening of novel 1,3-dioxolanes linked to N-5 of 5H-1,2,4-triazino[5,6-b]indole-3-thiol

Synthesis of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-indole-2,3-dione (10) was achieved by coupling 1H-indole-2,3-dione (16) with (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (15) in the presence of sodium hydride in dry N,N-dimethylformamide at room temperature in a closed Erlenmeyer flask. Condensation of 10 with hydrazinecarbothioamide in water afforded the thiosemicarbazone derivative 17; its subsequent cyclization with potassium carbonate in water gave the corresponding thione 18 in good yield. The 3-allylthio and 3-benzylthio derivatives 20 and 21 were also prepared by alkylating thiol 19 with alkyl halides in aqueous sodium hydroxide or coupling of 3-(allylthio/benzylthio)-5H-1,2,4-triazino[5,6-b]indoles (23 and 24) with compound 15 in NaH/DMF. Compound 20 was isomerized to a mixture of geometrical isomers (E/Z)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methyl]-3-(prop-1-en-1-ylthio)-5H-1,2,4-triazino[5,6-b]indoles (25 and 26), evidenced by their 1H- and 13C-NMR spectra taken in deuterodimethyl sulfoxide. Structural elucidation of the synthesized compounds was realized using FT-IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis. The newly synthesized compounds were found to possess moderate inhibitory activity against the fungus Candida albicans compared to clotrimazole as reference control. Compounds 10, 17, 19, 20, 21, 23 and 24 had mean growth inhibition zones (IZ) and minimal inhibitory concentrations (MIC) in the range of 12–15 mm and 31.25–200 μg mL-1, respectively, with inhibition levels in the range 70.58–88.23 %. Compound 19 exhibited moderate activity against Gram-positive bacteria Staphylococcus aureus relative to imipenem as the standard drug. All compounds were inactive against Escherichia coli and Pseudomonas aeruginosa.

COMPOUNDS AND COMPOSITIONS FOR RADIATION THERAPY AND METHODS OF USING THE SAME

The present disclosure relates to bisphenol ether derivatives and compositions thereof, which can be useful in radiation therapy for treatment of diseases, such as prostate cancer. In particular, the compounds of the present disclosure containing a radiolabeled atom can be useful in targeted delivery of radionuclides for treatment of lesions, tumors, and/or cancer cells.