138769-92-3 Usage
Description
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is a chiral chemical compound with the molecular formula C6H6I2O2. It is a dihydroxyiodobenzene isomer, characterized by the presence of two hydroxyl groups and two iodine atoms attached to a benzene ring. (+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE is significant in the field of organic chemistry due to its unique stereochemistry, featuring two stereocenters, and its potential applications in various industries.
Uses
Used in Organic Synthesis:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is utilized as a key intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is used as a chiral compound for the development of enantiomerically pure drugs. Its stereochemistry plays a crucial role in the biological activity of the resulting pharmaceuticals, ensuring targeted effects and minimizing side effects.
Used in Chemical Industry:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is employed in the chemical industry for the production of specialty chemicals, such as dyes, pigments, and polymers. Its unique properties contribute to the development of innovative materials with specific characteristics, catering to various applications.
Used in Asymmetric Synthesis:
As a chiral compound with two stereocenters, (+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is used in asymmetric synthesis to produce enantiomerically enriched products. This is crucial for the development of single-enantiomer drugs, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Chiral Ligand Development:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is also used in the development of chiral ligands for catalysis. These ligands are essential in enantioselective catalysis, enabling the production of enantiomerically pure compounds with high selectivity and efficiency.
Check Digit Verification of cas no
The CAS Registry Mumber 138769-92-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,7,6 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 138769-92:
(8*1)+(7*3)+(6*8)+(5*7)+(4*6)+(3*9)+(2*9)+(1*2)=183
183 % 10 = 3
So 138769-92-3 is a valid CAS Registry Number.
138769-92-3Relevant articles and documents
Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin
Baidilov, Daler,Rycek, Lukas,Trant, John F.,Froese, Jordan,Murphy, Brennan,Hudlicky, Tomas
, p. 10994 - 10998 (2018/06/04)
Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.
Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes
Boyd, Derek R.,Sharma, Narain D.,Byrne, Breige,Hand, Mark V.,Malone, John F.,Sheldrake, Gary N.,Blacker, John,Dalton, Howard
, p. 1935 - 1943 (2007/10/03)
Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.
Enzymatic and Chemical Syntheses of cis-Dihydrodiol Derivatives of Monocyclic Arenes
Boyd, Derek R.,Hand, Mark V.,Sharma, Narain D.,Chima, Jagdeep,Dalton, Howard,Sheldrake, Gary N.
, p. 1630 - 1632 (2007/10/02)
Metabolism of bromobenzene and iodobenzene by growing cultures of Pseudomonas putida UV4 gave the corresponding cis-dihydrodiol products 1 and 2 in high yields; subsequent direct chemical substitution of the halogen atoms in these metabolites provided a new range of enantiomerically pure cis-dihydrodiols of known absolute configuration.
