BIOMAT Database Logo BIOMAT Database Logo

Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines. 2016

Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, P. R. China.

With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were obtained in 86-99% yields, >20:1 dr, and 94 → 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when α-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results.

UI MeSH Term Description Entries
D009705 Nucleosides Purine or pyrimidine bases attached to a ribose or deoxyribose. (From King & Stansfield, A Dictionary of Genetics, 4th ed) Nucleoside,Nucleoside Analog,Nucleoside Analogs,Analog, Nucleoside,Analogs, Nucleoside
D011687 Purines A series of heterocyclic compounds that are variously substituted in nature and are known also as purine bases. They include ADENINE and GUANINE, constituents of nucleic acids, as well as many alkaloids such as CAFFEINE and THEOPHYLLINE. Uric acid is the metabolic end product of purine metabolism.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D061565 Cycloaddition Reaction Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction
D020650 Combinatorial Chemistry Techniques A technology, in which sets of reactions for solution or solid-phase synthesis, is used to create molecular libraries for analysis of compounds on a large scale. Chemistry Techniques, Combinatorial,Techniques, Combinatorial Chemistry,Chemistry Technic, Combinatorial,Chemistry Technics, Combinatorial,Chemistry Technique, Combinatorial,Combinatorial Chemistry Technic,Combinatorial Chemistry Technics,Combinatorial Chemistry Technique,Technic, Combinatorial Chemistry,Technics, Combinatorial Chemistry,Technique, Combinatorial Chemistry

Related Publications

Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
SYNTHESIS OF POTENTIAL ANTINEOPLASTIC AGENTS. XXXI. 9-ALKYL-9H-PURINES.
July 1962, Journal of medicinal and pharmaceutical chemistry,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Highly Chemoselective Synthesis of Purino[3,2-c]oxazoles via the Asymmetric Dearomative [3+2] Cycloaddition of Purines with Donor-Acceptor Oxiranes.
October 2022, Organic letters,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition.
December 2014, Nature communications,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Asymmetric synthesis of cyclohexene nucleoside analogues.
October 2011, The Journal of organic chemistry,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Synthesis and antirhinovirus activity of 6-(dimethylamino)-2-(trifluoromethyl)-9-(substituted benzyl)-9H-purines.
August 1989, Journal of medicinal chemistry,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Synthesis and anticancer activity of (RS)-9-(2,3-dihydro-1,4-benzoxaheteroin-2-ylmethyl)-9H-purines.
September 2011, European journal of medicinal chemistry,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
[Acyclic nucleoside analogues. III. Synthesis of new 2',3'-dideoxy-2',3'-didehydronucleoside analogues].
January 2004, Bioorganicheskaia khimiia,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines.
May 1990, Journal of medicinal chemistry,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Synthesis and anticancer activity of (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines.
January 2008, ChemMedChem,
Dan-Jie Zhang, and Ming-Sheng Xie, and Gui-Rong Qu, and Yao-Wei Gao, and Hai-Ming Guo
Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates.
March 2012, Organic letters,
Copied contents to your clipboard!