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Synthesis of Glycomimetics by Diastereoselective Passerini Reaction


Vlahoviček-Kahlina, Kristina; Vazdar, Mario; Jakas, Andreja; Smrečki, Vilko; Jerić, Ivanka
Synthesis of Glycomimetics by Diastereoselective Passerini Reaction // Journal of organic chemistry, 83 (2018), 21; 13146-13156 doi:10.1021/acs.joc.8b01874 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis of Glycomimetics by Diastereoselective Passerini Reaction

Autori
Vlahoviček-Kahlina, Kristina ; Vazdar, Mario ; Jakas, Andreja ; Smrečki, Vilko ; Jerić, Ivanka

Izvornik
Journal of organic chemistry (0022-3263) 83 (2018), 21; 13146-13156

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Multicomponent reactions, Passerini reaction. D-fructose, glycomimetics

Sažetak
We describe the utilization of bis-isopropylidene-protected d-fructose-derived aldehyde in the Passerini reaction with various acids and isocyanides. A library of densely functionalized glycomimetics bearing up to 3 carbohydrate units was obtained in high yields and diastereoselectivities. The configuration of the newly formed stereocenter was determined and the diastereoselectivity was rationalized by DFT calculations.

Izvorni jezik
Engleski



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-3102 - Višekomponentne reakcije u sintezi peptidnih mimetika (IVANKA JERIĆ, )

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • Arts & Humanities Citation Index (A&HCI)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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