Convenient preparation of perbenzylated 2-Azido and 2-N-acetylamino-2-deoxy-D-hexono-1,5-lactones by oxidation of the corresponding lactols

Article abstract of DOI:10.1080/07328309608005438

2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).

Full text of DOI:10.1080/07328309608005438

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Convenient Preparation of
Perbenzylated 2-Azido and 2-N-
Acetylamino-2-Deoxy-d-Hexono-1,5-
Lactones by Oxidation of the
Corresponding Lactols
Ebtissam Ayadi a , Stanislas Czernecki a & Juan Xie a
a Université Pierre et Marie Curie, Laboratoire de Chimie des
Glucides , 4, place Jussieu, 75005, Paris, France
Published online: 22 Aug 2006.
To cite this article: Ebtissam Ayadi , Stanislas Czernecki & Juan Xie (1996) Convenient
Preparation of Perbenzylated 2-Azido and 2-N-Acetylamino-2-Deoxy-d-Hexono-1,5-Lactones by
Oxidation of the Corresponding Lactols, Journal of Carbohydrate Chemistry, 15:2, 191-199, DOI:
10.1080/07328309608005438
To link to this article: http://dx.doi.org/10.1080/07328309608005438
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