20462-00-4

Usage

Uses

Used in Organic Synthesis:
Ethyl 1,3-dithiane-2-carboxylate is used as a reagent in organic synthesis for its ability to participate in syn-selective aldol reactions. This makes it a valuable tool for creating complex molecular structures with specific stereochemistry.
Used in Asymmetric Oxidation:
The compound is used as a substrate in asymmetric oxidation reactions, which can produce trans bis-sulfoxide with a yield of up to 60%. This application is particularly relevant in the field of pharmaceuticals and materials science, where the control of stereochemistry is crucial for the development of effective and selective compounds.
Used in the Preparation of α-Keto Esters:
Ethyl 1,3-dithiane-2-carboxylate is used as a precursor to generate carbanion, which finds application in the preparation of α-keto esters. These esters are important intermediates in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in the Pharmaceutical Industry:
Ethyl 1,3-dithiane-2-carboxylate is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its ability to participate in selective reactions and generate specific intermediates makes it a valuable asset in the development of new drugs and therapies.
Used in the Chemical Research Industry:
In the field of chemical research, Ethyl 1,3-dithiane-2-carboxylate is used as a model compound to study reaction mechanisms and develop new synthetic methodologies. Its unique reactivity and properties allow researchers to explore novel approaches to organic synthesis and expand the scope of chemical reactions.

Synthesis Reference(s)

Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615

Purification Methods

Dissolve the ester in CHCl3, wash with aqueous K2CO3, twice with H2O, dry over MgSO4, filter, evaporate and distil the residue. [Eliel & Hartman J Org Chem 37 505 1972, Seebach Synthesis 1 17 1969, Beilstein 19/7 V 227.]

InChI:InChI=1/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3

Upstream product

• 109-80-8 1.3-propanedithiol 
• 535-15-9 ethyl 1,1-dichloroacetate 
• 6065-82-3 Ethyl diethoxyacetate 
• 515-84-4 Ethyl trichloroacetate 
• 64805-08-9 ethyl glyoxylate hydrate 

Downstream Products

• 58810-96-1 2-[4-(5,5-dimethyl-4,5-dihydro-oxazol-2-yl)-benzyl]-[1,3]dithiane-2-carboxylic acid ethyl ester 
• 32557-27-0 ethyl 2-butyl-1,3-dithiane-2-carboxylate 
• 83559-51-7 2-(3-Phenyl-2-propenyl)-1,3-dithian-2-carbonsaeure-ethylester 
• 125443-02-9 2-(2-Benzyloxy-4,6-dichloro-benzyl)-[1,3]dithiane-2-carboxylic acid ethyl ester 
• 90626-79-2 2L-(2,3,5/4)-4-O-Benzyl-5-(2-ethoxycarbonyl-1,3-dithian-2-yl)-2,3-O-isopropyliden-2,3,4-trihydroxycyclohexanon 
• 20461-89-6 1,3-dithiane-2-carboxylic acid 
• 83559-50-6 2-(3-Nitrobenzyl)-1,3-dithian-2-carbonsaeure-ethylester 
• 83559-49-3 2-(4-Nitrobenzyl)-1,3-dithian-2-carbonsaeure-ethylester 
• 173065-80-0 ethyl 4,5-di-O-benzyl-3-deoxy-L-threo-2-hexulosonate 2-(1,3-propanediyldithioacetal) 
• 34906-12-2 2-formyl-1,3-dithiane 

Relevant academic research and scientific papers

A new synthesis of 2-substituted-1,3-dithianes from trichloromethyl compounds

Trichloromethyl compounds are efficiently converted into 1,3-dithianes upon reaction with a disodium 1,3-propanedithiolate-1,3-propanedithiol mixture in DMF solution at 0 °C. This synthesis is limited to those substrates where the substituent attached to the trichloromethyl group is an electron-withdrawing group.

INHIBITORS OF CBL-B AND METHODS OF USE THEREOF

Compounds, compositions, and methods for use in inhibiting the E3 enzyme Cbl-b in the ubiquitin proteasome pathway are disclosed. The compounds, compositions, and methods can be used to modulate the immune system, to treat diseases amenable to immune system modulation, and for treatment of cells in vivo, in vitro, or ex vivo.

PYRIDAZINONE COMPOUNDS

The invention is directed to pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

PREPARATION OF IMIDAZOLE DERIVATIVES AND METHODS OF USE

This invention relates to imidazole compounds which are useful in promoting smoking cessation and maintaining abstinence.

Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for cholesterol ester hydrolase

Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of α-difluoro-β-trifluoroketo-(5,10,15) and of α-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates.

AN EFFICIENT ROUTE TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) DERIVATIVES VIA A 1,4-CYCLIC SULFATE APPROACH

Treatment of 2,3:5,6-di-O-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate.Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4,5:7,8-di-O-isopropylidene-3-deoxy-α(β)-D-manno-2-octulosonate in an excellent yield.

CLAY CATALYSIS: SYNTHESIS OF ORGANOSULPHUR SYNTHONS

The Montmorillonite KSF catalyses the synthesis of a large variety of organic sulphur compounds from carbonyl compounds: dithianes, thioacetals, thioketals,thiochromanes.

Synthetic approaches to haplophytine. 1. Synthesis of 1-methoxy- and 1-hydroxy-6-phenyl-6-(2-pivaloylamidophenyl)non-8-ene-4,5-dione and 1-methyl-3-phenyl-3-(pivaloylamidophenyl)-2-pyrrolidinone

An analysis of the structures of the alkaloid haplophytine and its dihydrobromide which is formed with rearrangement, shows that they are both derived from a 7-(2-amino-3-hydroxyphenyl)-7-aryl-9-(methylamino)-5,6-dioxonoanoic acid moiety (3).Approaches to the synthesis of compounds related to 3 are described.The dianion 13 of phenyl(2-pivaloylamidophenyl)methane, that of methyl 2-phenyl-2-(2-pivaloylamidophenyl)acetate, and the trianion 37 of 2-phenyl-2-(2-pivaloylamidophenyl)acetic acid undergo C-alkylation and C-acylation with nucleophiles.Acylation of 13 with methyl 2,2,5-trimethoxypentanoate followed by hydrolysis gives 6-methoxy-1-phenyl-1-(2-pivaloylamidophenyl)-2,3-hexanedione.This with allyl bromide and sodium carbonate gives O-allyl derivative, which on thermolysis is converted to its C-allyl isomer, 1-methoxy-6-phenyl-6-(2-pivaloylamidophenyl)non-8-ene-4,5-dione.The corresponding 1-hydroxy compound was prepared analogously via acylation of 13 with methyl tetrahydro-2-methoxyfuran-2-carboxylate.C-allylation of trianion 37 gives 2-phenyl-2-(2-pivaloylamidophenyl)pent-4-enoic acid, whose methyl ester on ozonolysis followed by treatment with methylamine hydrochloride and sodium cyanoborohydride gives 1-methyl-3-phenyl-3-(2-pivaloylamidophenyl)-2-pyrrolidinone, a potential advanced intermediate for the synthesis of compounds related to 3.

Preparation and Reactions of Some Reagents for Umpolung under Phase-transfer Catalysis

Thioacetals 4a-h are used as reagents for umpolung.They can be prepared in high yields from inexpensive starting materials under phase-transfer catalysis (PTC).H/D-exchange reactions of thioacetals under PTC-conditions are described.Ethyl 1,3-dithiane-2-carboxylate (4a) served as a model compound in order to demonstrate possibilities and limitations of PTC-deprotonation and subsequent reaction with electrophiles compared with other procedures.