Stereoselective synthesis of nicotinamide beta-riboside and nucleoside analogs.
The beta-anomers of N-ribofuranosylnicotine-3-carboxamide (beta-NAR) and its nicotinic acid analog (beta-NaR) were obtained by stereoselective synthesis via glycosylation of the presilylated bases under Vorbruggen's protocol. A NAR analog, methylated in position 3 of the ribosylic moiety, is also reported.
Franchetti
Palmarisa
P
Dipartimento di Scienze Chimiche, Università di Camerino, 62032 Camerino, Italy. palmarisa.franchetti@unicam.it
Pasqualini
Michela
M
Petrelli
Riccardo
R
Ricciutelli
Massimo
M
Vita
Patrizia
P
Cappellacci
Loredana
L
D006031:Glycosylation; D009536:Niacinamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011726:Pyridinium Compounds; D013237:Stereoisomerism
D009705:Nucleosides; D011726:Pyridinium Compounds; C018613:nicotinamide-beta-riboside; D009536:Niacinamide