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001-es BibID:	BIBFORM102250
035-os BibID:	(cikkazonosító)3422 (WoS)000809478500001 (Scopus)85131644032
Első szerző:	Demeter Fruzsina (okleveles vegyész)
Cím:	Synthesis of Four Orthogonally Protected Rare L-Hexose Thioglycosides from D-Mannose by C-5 and C-4 Epimerization / Fruzsina Demeter, Ilona Bereczki, Anikó Borbás, Mihály Herczeg
Dátum:	2022
ISSN:	1420-3049
Megjegyzések:	l-Hexoses are important components of biologically relevant compounds and precursors of some therapeuticals. However, they typically cannot be obtained from natural sources and due to the complexity of their synthesis, their commercially available derivatives are also very expensive. Starting from one of the cheapest d-hexoses, d-mannose, using inexpensive and readily available chemicals, we developed a reaction pathway to obtain two orthogonally protected l-hexose thioglycoside derivatives, l-gulose and l-galactose, through the corresponding 5,6-unsaturated thioglycosides by C-5 epimerization. From these derivatives, the orthogonally protected thioglycosides of further two l-hexoses (l-allose and l-glucose) were synthesized by C-4 epimerization. The preparation of the key intermediates, the 5,6-unsaturated derivatives, was systematically studied using various protecting groups. By the method developed, we are able to produce highly functionalized l-gulose derivatives in 9 steps (total yields: 21-23%) and l-galactose derivatives in 12 steps (total yields: 6-8%) starting from d-mannose.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban folyóiratcikk L-hexoses thioglycosides epimerization elimination hydroboration
Megjelenés:	Molecules. - 27 : 11 (2022), p. 1-35. -
További szerzők:	Bereczki Ilona (1981-) (vegyész, antibiotikumkémikus) Borbás Anikó (1965-) (vegyész) Herczeg Mihály (1979-) (vegyész, biológia-kémia tanár)
Pályázati támogatás:	PPD 461038 MTA K 132870 OTKA FK 137924 OTKA GINOP-2.3.4?15?2020?00008 GINOP
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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