1,2-Oxazoline, carbohydrate derivatives

Carbohydrate derivs. A soln. of methyl 2-benzamido-3,6-di-0-benzoyl-2-deoxy-4-0-mesyl-a-D-glucopyranoside in methylene chloride treated with a 1.6 N Na-methoxide soln., and allowed to stand 20 hrs. at room temp. methyl 2,3-dide-oxy-3,2-(2-phenyl-l-oxa-3-azaprop-2-eno)-a-D-gulopyranoside. Y 77-95%. M.W. Horner, L. Hough, and A. C. Richardson, Soc. (C) 1971, 99 zl -oxazoline ring with FeClg s. K. L. Matta and O. P. Bahl, Carbohyd. Res. 21, 460 (1972). 

From a structural point view, the most explored thionocarbamates in carbohydrate chemistry are five-membered l,3-oxazolidine-2-thiones.27 29 With respect to the synthesis of aromatic analogues of OZTs-1,3 oxazoline-2-thiones (OXTs), only two acyclic D-fructose-derived OXTs were recently reported by Rollin and co-workers.30... 

The first recorded use of carbohydrates as templates for the synthesis of the sphingosine bases was for the preparation of A-benzoylphytosphingosine (6) [34, 35]. The oxazoline derivative (1) which is readily prepared from D-glucosamine [36] was con-... 

Abstract The high synthetic versatiUty exhibited by the isothiocyanato motif has allowed its use as a building block in the preparation of a plethora of derivatives. When present in carbohydrates, the strong electrophilicity shown by isothiocyanates, together with the possibility of undergoing cycloaddition reactions has made it possible to access a broad spectrum of heterocyclic compounds, of either synthetic or pharmaceutical interest. Among them, noteworthy are 1,3-oxazolidine- and l,3-oxazinane-2-thiones (cyclic thiocarbamates), 2-amino-2-oxazolines (cyclic isoureas), 2-amino-2-thiazolines (cyclic isothioureas), nucleosides, and spironucleosides. 

Glycosylation with carbohydrate zl -oxazoline derivs. s, 14,174 suppl. 29... 

I, 218-20 suppl. 29 Glycosylation with carbohydrate A -oxazoline derivs. 14,174... 

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