20461-99-8 Usage
Description
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE is an α-keto acid equivalent with significant synthetic utility in organic chemistry. It is characterized by its ability to participate in conjugate additions to enones and undergo syn-selective aldol reactions, making it a bulky equivalent of acetate. The anion derived from this compound acts as a nucleophile in various total syntheses of complex alkaloids, such as dihydrocorynantheol, tacamonine, rhynchophylline, and hirsutine. Additionally, it is involved in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams. ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE is a clear light yellow liquid.
Uses
Used in Pharmaceutical Synthesis:
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE is used as a synthetic building block for the development of complex alkaloids, such as dihydrocorynantheol, tacamonine, rhynchophylline, and hirsutine. Its unique reactivity and selectivity in conjugate additions and aldol reactions make it a valuable tool in the synthesis of these bioactive compounds, which have potential applications in the treatment of various diseases and conditions.
Used in Organic Chemistry Research:
As an α-keto acid equivalent, ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE is used as a key intermediate in the development of new synthetic methods and strategies in organic chemistry. Its ability to undergo syn-selective aldol reactions and participate in nucleophilic reactions makes it a versatile building block for the creation of novel molecular structures with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.
Used in the Synthesis of Bioactive Molecules:
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE is used as a synthetic precursor for the development of bioactive molecules with potential applications in the pharmaceutical industry. Its unique reactivity allows for the creation of complex molecular structures that can be further modified and optimized for specific biological targets, leading to the discovery of new drugs and therapeutic agents.
Used in the Development of Novel Drug Delivery Systems:
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE can be used as a component in the design and synthesis of novel drug delivery systems, such as nanoparticles and other carriers, to improve the bioavailability and therapeutic outcomes of various drugs. Its unique chemical properties and reactivity make it a promising candidate for the development of innovative drug delivery platforms.
Purification Methods
Dissolve the ester in CHCl3, wash it with aqueous K2CO3, twice with H2O, dry it over MgSO4, filter, evaporate and distil the residue in vacuo. [Hermann et al Tetrahedron Lett 2599 1973, Corey & Erickson J Org Chem 36 3553 1971]. [Beilstein 19/7 V 225.]
Check Digit Verification of cas no
The CAS Registry Mumber 20461-99-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,4,6 and 1 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 20461-99:
(7*2)+(6*0)+(5*4)+(4*6)+(3*1)+(2*9)+(1*9)=88
88 % 10 = 8
So 20461-99-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3
20461-99-8Relevant articles and documents
Preparation and Reactions of Some Reagents for Umpolung under Phase-transfer Catalysis
Lissel, Manfred
, p. 1589 - 1601 (2007/10/02)
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.
