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Atomistic dynamics of elimination and substitution driven by entrance channel.
J Chem Phys
January 2025
Key Laboratory of Chemistry and Chemical Engineering on Heavy-Carbon Resources, School of Chemistry and Chemical Engineering, Yili Normal University, Yining 835000, People's Republic of China.
E2 elimination and SN2 substitution reactions are of central importance in preparative organic synthesis due to their stereospecificity. Herein, atomistic dynamics of a prototype reaction of ethyl chloride with hydroxide ion are uncovered that show strikingly distinct features from the case with fluoride anion. Chemical dynamics simulations reproduce the experimental reaction rate and reveal that the E2 proceeding through a direct elimination mechanism dominates over SN2 for the hydroxide ion reaction.
View Article and Find Full Text PDFAcquiring stereospecific new pseudosugars: Obtaining rac-decahydro-1,4-epoxynaphthalene-2,3,5,6,7,8-hexaols from the Diels-Alder reaction and investigating their biological effects.
Bioorg Chem
January 2025
Sakarya University, Faculty of Arts and Sciences, Chemistry Department, 54050, Sakarya, Turkey. Electronic address:
In this study, Diels-Alder reaction was performed to sulfolene and endo/exo-diacetate compounds. After a series of reactions, new conduritol A and F analogs containing oxo-bridge and naphthalene rings in their structures were synthesized. To the starting compound, bromination, elimination, singlet oxygen reaction, acetylation, selective oxidation with osmium tetroxide (OsO), and m-chloroperbenzoic acid (m-CPBA), re-acetylation, and finally hydrolysis of the compounds by NH(g)/MeOH reactions were carried out.
View Article and Find Full Text PDFMetal Additive-Free Iodine-Promoted Reorganization of Ynamide-Ynes and Stereoselective 1,2-Diiodination.
Chem Asian J
November 2024
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100 Shiquan 1st Rd, Sanmin District, Kaohsiung City, 807, Taiwan.
We report a metal additive-free iodine-promoted one-step structural reorganization of ynamide-ynes and simultaneous stereoselective 1,2-diiodination of the migrated alkyne to form stereospecific tetrasubstituted alkenyl diiodo-tethered indoles (E-isomer). Molecular iodine is cost effective, user friendly, less toxic, commercially available, and easy to handle. The key features of the reaction include metal-and additive-free environment, selectivity, structural reorganization, mild reaction conditions, simple workup, and gram-scale synthesis.
View Article and Find Full Text PDFSynthesis of branched and linear galactooligosaccharides related to glucuronoxylomannogalactan of .
Front Chem
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Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
This study focuses on the synthesis of a series of oligo--(1→6)-D-galactopyranosides bearing -D-galactofuranosyl residues at O-2 and/or O-3, which relate structurally to fragments of glucuronoxylomannogalactan (GXMGal) from the fungal pathogen that causes severe diseases in immunocompromised patients. The preparation of target compounds is based on the use of a selectively O-protected N-phenyltrifluoroacetimidoyl galactopyranoside donor with an allyl group at O-2, levulinoyl group (Lev) at O-3, pentafluorobenzoyl (PFB) group at O-4, and fluorenylmethoxycarbonyl (Fmoc) group at O-6. The choice of protecting groups for this donor ensures the stereospecific formation of (1→6)-glycosidic bonds due to the stereodirecting effect of acyls at O-3, O-4, and O-6.
View Article and Find Full Text PDFEnantiomorphic Site-Assisted Chain End Control Stereospecific Alternating Copolymerization of Chiral Cyclic Diesters.
Angew Chem Int Ed Engl
October 2024
State Key Laboratory of Applied Organic Chemistry (Lanzhou University), Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
Stereospecific alternating copolymerization of different chiral cyclic esters is one feasible approach to enrich the structural diversity of copolyesters and tailor their properties. However, dramatically different reactivities of different cyclic esters let a perfectly stereospecific alternating polymerization of these cyclic esters be a challenge, thus the catalyst is required to balance their reactivities. Herein, a remarkable enantiomorphic site effect on chain end control was discovered and successfully utilized to balance the reactivities of highly reactive S, S-lactide (S, S-LA) and low reactive R, R-ethylglycolide (R, R-EG)/R, R-propylglycolide (R, R-PG) during their heterospecific alternating copolymerization.
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