P. Barili, G. Berti, G. Catelani
Jul 1, 1989
Citations
0
Influential Citations
20
Citations
Journal
Carbohydrate Research
Abstract
Treatment of O-protected 3,4-O-isopropylidene-β-d-galactopyranosides with tert-BuOK in N,N-dimethylformamide or methyl sulfoxide produces 4-deoxy-α-l-threo-hex-4-enopyranosides in good yields. The corresponding α-anomers and the non-O-protected derivatives are resistant to this treatment. Reaction of methyl 4-deoxy-2,6-di-O-methyl-α-l-threo-hex-4-enopyranoside with 3-chloroperbenzoic acid in CH2Cl2 gave a crystalline adduct that was hydrolyzed to 2,6-di-O-methyl-l-arabino-hexos-5-ulose.