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001-es BibID:	BIBFORM023228
Első szerző:	Somsák László (vegyész)
Cím:	A new, scalable preparation of a glucopyranosylidene-spiro-thiohydantoin : one of the best inhibitors of glycogen phosphorylases / László Somsák, Veronika Nagy
Dátum:	2000
Megjegyzések:	Benzobromo-glucose was converted into per-O-benzoylated beta-d-glucopyranosyl cyanide by mercury(II)cyanide in nitromethane. Partial hydrolysis of the nitrile with hydrogen bromide in acetic acid gave per-O-benzoylated C-(beta-d-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-beta-d-gluco-pyranosyl cyanide and C-(1-bromo-1-deoxy-beta-d-glucopyranosyl)formamide. Reaction of the latter with ammonium thiocyanate in nitromethane gave the per-O-benzoylated C-6S configured glucopyranosylidene-spiro-thiohydantoin together with a small amount of the per-O-benzoylated C-(1-hydroxy-beta-d-gluco-pyranosyl)formamide. Debenzoylation of the spiro-thiohydantoin with sodium methoxide in methanol gave gram amounts of the title inhibitor. The described sequence should be suitable for scaling up and the target compound can be prepared in ~30% overall yield starting from d-glucose.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:	Tetrahedron: Asymmetry. - 11 : 8 (2000), p. 1719-1727. -
További szerzők:	Nagy Veronika
Internet cím:	Intézményi repozitóriumban (DEA) tárolt változat
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