37002-45-2

Usage

Uses

Used in Coordination Chemistry:
In the field of coordination chemistry, (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL is used as a ligand for the synthesis of (R,R)-DIPPOP complexes. Its unique structure allows it to form stable coordination compounds with metal ions, which are of significant interest in various research areas, including catalysis and materials science.
Used in Pharmaceutical Industry:
(-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to form stable complexes with metal ions makes it a valuable building block for the development of new drugs with improved properties, such as enhanced bioavailability and targeted delivery.
Used in Material Science:
In material science, (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL is used as a component in the development of novel materials with specific properties. Its coordination chemistry capabilities enable the creation of materials with tailored characteristics, such as improved mechanical strength, thermal stability, or electrical conductivity.
Used in Analytical Chemistry:
(-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL is used as a reagent in analytical chemistry for the detection and quantification of various compounds. Its unique chemical properties make it a valuable tool for the development of new analytical methods and techniques.

InChI:InChI=1/C21H26O8S2/c1-15-5-9-17(10-6-15)30(22,23)26-13-19-20(29-21(3,4)28-19)14-27-31(24,25)18-11-7-16(2)8-12-18/h5-12,19-20H,13-14H2,1-4H3

Upstream product

• 153059-36-0 3,4-O-isopropylidene-L-mannitol 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 98-59-9 p-toluenesulfonyl chloride 
• 87-69-4 L-Tartaric acid 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 83529-40-2 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylic acid 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 

Downstream Products

• 57495-46-2 (2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] 
• 99313-96-9 (4S,5S)-2,2-Dimethyl-4,5-bis-(2,3,5,6-tetramethyl-benzyl)-[1,3]dioxolane 
• 71359-99-4 (4R,5R)-4,5-Bis-{[bis-(2-methoxy-phenyl)-phosphanyl]-methyl}-2,2-dimethyl-[1,3]dioxolane 
• 122712-88-3 (-)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bisbutane 
• 122712-87-2 (R,R)-4,5-Bis-2,2-dimethyl-1,3-dioxolan 
• 78870-99-2 (R,R)-trans-4,5-bis<methyl>-2,2-dimethyl-1,3-dioxolane 
• 130502-12-4 (3aS,12aS)-2,2-Dimethyl-5,11-bis-(toluene-4-sulfonyl)-decahydro-1,3,8-trioxa-5,11-diaza-cyclopentacycloundecene 
• 130502-13-5 (3aS,15aS)-2,2-Dimethyl-5,14-bis-(toluene-4-sulfonyl)-dodecahydro-1,3,8,11-tetraoxa-5,14-diaza-cyclopentacyclotetradecene 
• 93834-41-4 (-)-2,3-O-isopropylidene-4-diphenylphosphino-1-O-tosyl-1,2,3-butanetriol 
• 130948-53-7 (4R,5R)-XYL-DIOP 
• 119580-48-2 (1S,2S)-1,2-O-isopropylidene-10-benzyl-4,7,13,16-tetraoxa-10-azacycloheptadecane 
• 119604-69-2 (1S,2S,6S,7S)-1,2,6,7-O-diisopropylidene-15-benzyl-4,9,12,18,21-pentaoxa-15-azacyclodocosane 
• 119604-68-1 (1S,2S,18S,19S)-1,2,18,19-O-diisopropylidene-10,27-dibenzyl-4,7,13,16,21,24,30,33-octaoxa-10,27-diazacyclotetratriacontane 
• 123135-92-2 Toluene-4-sulfonic acid (4S,5R)-5-[(di-m-tolyl-phosphanyl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis and electrochemical properties of a chiral silyl-substituted tetrathiafulvalene derivative

A new chiral tetrathiafulvalene (TTF) derivative and related silyl-substituted 1,3-dithiole-2-(thi)one compounds were synthesized and characterized by 1H NMR, 13C NMR, MS and IR spectra. Single crystal structure of the silyl-substituted 1,3-dithiole-2-one revealed the high degree of conjugation of the five-membered ring moiety in the compound. The electrochemical properties of the new TTF derivative were studied by cyclic voltammetry and the results indicated that the electron-donating ability of the chiral TTF derivative was similar to that of BEDT-TTF. The ΔE value for the new TTF derivative was smaller than those for TTF and BEDT-TTF, indicative of decreased Coulombic repulsion in the dicationic redox state. Formation of charge-transfer (CT) complex between the new donor and electron acceptor 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was demonstrated.

Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes

The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive (l)-(+)-tartaric acid and 4-methylstyrene is described. These helical structures were transformed into bis-iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre-catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.

Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles

A complementing Pd- and Rh-catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N-allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo-, regio- and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans-alkene selectivity is discussed.

Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition 'click-chemistry' in water

The synthesis of a new class of hybrid 1,2,3-triazozlo-δ-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition 'click-chemistry' reaction of various organic azides with an activated alkyne in water, followed by cyclization.

NEUROLOGICALLY-ACTIVE COMPOUNDS

The invention provides a compound of the formula (I): wherein R is methyl, ethyl, propyl, isopropyl, butyl, pentyl, neo-pentyl or cyclohexyl, or a salt or solvate thereof. These compounds are selective GABAC receptor antagonists. The invention also provides pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof. The invention also provides methods of enhancing the cognitive activity of an animal and methods of stimulating memory capacity in an animal, comprising the step of administering to the animal an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof.

Synthesis of chiral hydroxythiolanes as potential catalysts for asymmetric organozinc additions to carbonyl compounds

Optically active 3-hydroxythiolane was stereospecifically synthesized from L-aspartic acid and oxidized to give both diastereomeric S-oxides, which were chromatographicatly separated and their configuration was determined. Starting from natural (+)-(R,R)-tartaric acid, C2-symmetric trans-(R,R)-3,4-dihydroxythiolane was stereospecifically synthesized for the first time. Some of its monofunctionalized derivatives as well as its S-oxide were also obtained and characterized. meso-cis-3,4-Dihydroxythiolane was obtained in a similar way from meso-tartaric acid and subjected to desymmetrization either by a lipase-promoted acetylation or hydrolysis of the corresponding O, O'-diacetyl derivative, to give a chiral monoacetate with ee up to 36%. After its oxidation two diastereomeric sulfoxides were obtained which were separated by chromatography. The crystalline one was subjected to X-ray analysis and its absolute configuration was determined as 1S, 3S, 4R. All the optically active products were checked as potential catalysts for asymmetric addition of diethylzinc to benzaldehyde. However, they proved to have a very low catalytic activity: yields of the products were in the range 10-90% but ee only up to 10%. A conclusion was drawn that in this type of reaction neither is the hydroxy sulfide (sulfoxide) moiety capable of properly binding diethylzinc, nor does the sulfinyl group exert its normal stereoinduction.

Silver(I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers

(Matrix Presented) The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the difference in acidity between the two hydroxy groups, which undergo an intramolecular hydrogen bonding.

Total synthesis of koninginin D, B and E

Total synthesis of koninginin D, E and B was described. The structures of koninginin B and F, which were deduced as C4 epimer of koninginin E and D, respectively, have been corrected.

First total synthesis of (+)-koninginin D

A total synthesis of (+)-koninginin D (1) is described; the absolute configuration of the immediate antecedent of 1 is shown to have the configuration 7R,9S,10S by X-ray diffraction analysis.