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

Chemical Properties

white to cream crystalline powder

Uses

1,4-Di-O-tosyl-2,3-O-isopropylidene-L-threitol has been used in coordination chemistry of (R,R)-DIPPOP.

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 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 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 
• 87-69-4 L-Tartaric acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 

Downstream Products

• 57495-46-2 (2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] 
• 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 
• 122712-88-3 (-)-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 

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.