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A series of chiral sulfahydantoins have been synthesized by alkaline cyclization starting from N-sulfamylaminoacid methyl esters. Regioselective glycosylation of these pseudopyrimidic heterocycles was carried out with a benzyl protecting group on the N-sulfonylcarbamic position. Best glycosylation results were obtained by preliminary silylation of sulfahydantoins, and their condensation with a tetraacylribofuranose...
Syntheses of metal-free oxygen analogues of the sulfhemes-A and -C from protoporphyrin-IX dimethyl ester 1 are presented. Oxasulporphyrin-C dimethyl ester 5 is obtained by intramolecular displacement of a primary tosylate by a tertiary hydroxyl in an appropriately constructed precursor 18, or by surface-catalyzed rearrangement of the epoxide-bearing oxasulfporphyrin-A dimethyl ester 23. Compound23...
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