37002-45-2

Basic information

• Product Name: (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL
• Synonyms: trans-(-)-1,4-Di-O-tosyl-2,3-O-isopropylidene-L-threitol,97%;(2S,3S)-1,4-Di-O-tosyl-2,3-O-isopropylidene-L-threitol;(4S,5S)-(-)-4,5-Bis(tosyloxymethyl)-2,2-dimethyl-1,3-dioxolane (4S,5S)-(-)-2,2-Dimethyl-4,5-bis(tosyloxymethyl)-1,3-dioxide (4S,5S)-(-)-2,3-O-Isopropylidene-1,4-di-O-tosyl-L-threitol;((4S,5S)-2,2-diMethyl-1,3-dioxolane-4,5-diyl)bis(Methylene) bis(4-Methylbenzenesulfonate);(S,S)-(-)-2,3-O-Isopropylidenethreitol 1,4-ditosylate;4-Methylbenzenesulfonic acid [(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene) ester;(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol 4,5- Bis(4-methylbenzenesulfonate);(-)-1,4-Di-O-tosyl-2,3-O-isopropylidene-L-threitol
• CAS NO: 37002-45-2
• Molecular Formula: C₂₁H₂₆O₈S₂
• Molecular Weight: 470.56
• EINECS: 253-306-3
• Product Categories: organic compound;Biochemistry;Dioxanes & Dioxolanes;Dioxolanes;O-Substituted Sugars;Sugar Alcohols;Sugars
• Mol File: 37002-45-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 542.03°C (rough estimate)
• Flash Point: 321.7 °C
• Appearance: white/Powder
• Density: 1.3082 (rough estimate)
• Vapor Pressure: 4.31E-14mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DCM, Ethyl Acetate
• Stability: store cold
• BRN: 99610
• CAS DataBase Reference: (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL(37002-45-2)
• EPA Substance Registry System: (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL(37002-45-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 37002-45-2(Hazardous Substances Data)

Usage

Description

(-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL, also known as 1,4-di-O-tosyl-2,3-O-isopropylidene-L-threitol, is a white to cream crystalline powder with unique chemical properties. It is a complex organic compound that has found applications in various fields due to its distinctive characteristics.

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 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 83529-40-2 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylic acid 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 

Downstream Products

• 57495-46-2 (2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] 
• 137129-41-0 (+)-(4S-trans)-<4,5-dimethanol-2,2-dimethyl-1,3-dioxolane>-bis<3-(2-bromo)pyridine> 
• 125518-43-6 tetrakisbisphosphine 
• 122712-88-3 (-)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bisbutane 
• 53170-35-7 cyclodiop 
• 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 
• 122712-87-2 (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 

Relevant articles and documents

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.

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.