THE USE OF N-ALKOXYCARBONYL DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE AS DONORS IN GLYCOSYLATION REACTIONS

1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-d-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-a-d-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group. © 1990.