Benzobromo-glucose was converted into per-O-benzoylated β-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-(β-D-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-β-D-glucopyranosyl cyanide and C-(1-bromo-1-deoxy-β-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-β-D-glucopyranosyl)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. (C) 2000 Elsevier Science Ltd.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry