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2004
Nucleic acids
U 0700
Stereoselective Synthesis of Nicotinamide β-Riboside and Nucleoside Analogues.
The key elements of the stereoselective synthesis of nicotinamide and nicotinic acid
52- 183 —
β-ribosides (V) involve the formation of silylated nicotinic bases and their coupling
with protected sugars (II) under Vorbruggen's conditions in the presence of a catalytic
amount of Tms-O-Tf. This method, carried out under controlled conditions, provide
only the β-anomers (IV). Basic hydrolytic deblocking of (IV) at low temperature minimizes cleavage of the glycosidic linkage to afford the desired targets (V) as white solids after purification. — (FRANCHETTI*, P.; PASQUALINI, M.; PETRELLI, R.;
RICCIUTELLI, M.; VITA, P.; CAPPELLACCI, L.; Bioorg. Med. Chem. Lett. 14
(2004) 18, 4655-4658; Dip. Sci. Chim., Univ. Camerino, I-62032 Camerino, Macerata,
Italy; Eng.) — H. Hoennerscheid
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