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

Article Article scientifique Article Synthesis and structural assignement of 1-O-acetyl-2,3,5-tri-O- benzoyl-4-(thymin-1-YL)-α-L-Lyxofuranose eng 1995 author Grouiller Annie 27089 author Uteza Valérie author Komaromi Istvan 27773 author Tronchet Jean Marcel Julien 25054 1387-1391 10.1080/07328309508005419 0732-8303 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). Dewey 615 31 Section des sciences pharmaceutiques 17 false Journal of carbohydrate chemistry 14 9 96204f11-376d-4ff5-8f8c-9bf01681fac8 Article (Published version) Restricted GROUILLER_JCC_13911995.pdf 1857983 application/pdf restrictedAccess Faculté des sciences / Section des sciences pharmaceutiques

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Synthesis and structural assignement of 1-O-acetyl-2,3,5-tri-O- benzoyl-4-(thymin-1-YL)-α-L-Lyxofuranose	Journal of carbohydrate chemistry			1995	124	0

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Grouiller, Annie