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001-es BibID:	BIBFORM008744
Első szerző:	Czifrák Katalin (vegyész)
Cím:	Synthesis of anomeric sulfonamides and their behaviour under radical-mediated bromination conditions / Katalin Czifrák, László Somsák
Dátum:	2009
Megjegyzések:	O-Peracetylated methyl 3-(D-glycopyranosylthio)propanoates of beta-D-gluco, and alpha- and beta-D-galacto configurations were oxidized to the corresponding S,S-dioxides (sulfones) by Oxone(R) or MCPBA. Oxidation of the beta-D-gluco derivative with H2O2/Na2WO4 gave the corresponding S-oxide (sulfoxide). DBU-induced elimination of methyl acrylate from the beta-D-gluco and beta-D-galacto configured S,S-dioxides (sulfones) gave O-peracetylated beta-D-glycopyranosyl-1-C-sulfinates which, on treatment with H2NOSO3H, furnished the corresponding beta-D-glycopyranosyl-1-C-sulfonamides. Radical-mediated bromination of the protected methyl 3-(beta-D-glycopyranosylthio)propanoate S,S-dioxides gave mixtures of 1-C- and 5-C-bromoglycosyl compounds. Similar brominations of the O-peracetylated beta-D-glycopyranosyl-1-C-sulfonamides resulted in the formation of a-D-glycopyranosyl bromides and 1-C- and 5-C-bromoglycosyl sulfonamides. A rationale for these observations was proposed. Methyl 3-(beta-D-glucopyranosylthio)propanoate, its S,S-dioxide, and beta-D-glucopyranosyl-1-C-sulfonamide proved inefficient when tested as inhibitors of rabbit muscle glycogen phosphorylase b.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban Sulfonamide Glycopyranosyl Bromination Radical
Megjelenés:	Carbohydrate Research. - 344 : 3 (2009), p. 269-277. -
További szerzők:	Somsák László (1954-) (vegyész)
Internet cím:	DOI elektronikus változat
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