Scientific article

Synthesis and structural assignement of 1-O-acetyl-2,3,5-tri-O- benzoyl-4-(thymin-1-YL)-α-L-Lyxofuranose

Published inJournal of carbohydrate chemistry, vol. 14, no. 9, p. 1387-1391
Publication date1995

Analogues of nucleosides in which the nucleobase is fixed onto the C-4 of the sugar moiety are generally prepared either from 4,5-unsaturated sugar derivatives or via a formaldehyde condensation.1 We tested the furanosyl bromide reactivity of 12 towards a series of nucleophiles, mostly azides or cyanides, without success. Conversely, the nucleosidation of 1 using 5-methyl-2,4-bis(trimethyl-silyloxy)pyrimidine in the presence of stannic chloride took place at the second anomeric position (C-4) and led to the isolation in acceptable yield (47%) of a unique anomer 2 (Scheme 1).

Citation (ISO format)
GROUILLER, Annie et al. Synthesis and structural assignement of 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>- benzoyl-4-(thymin-1-YL)-α-L-Lyxofuranose. In: Journal of carbohydrate chemistry, 1995, vol. 14, n° 9, p. 1387–1391. doi: 10.1080/07328309508005419
Main files (1)
Article (Published version)
ISSN of the journal0732-8303

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