Synthesis and X-ray crystallographic study of cyclobis-(1 → 2)-α-D-glucopyranosyl peracetate

Article abstract of DOI:10.1016/S0008-6215(97)00153-5

Treatment of O-(3,4,6-tri-O-acetyl-2-O-benzyl- α-D-glucopyranosyl)-(1 → 2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate with BF₃·Et₂O gave a high yield of the peracetate of cyclobis-(1 → 2)-α-D-glucopyranosyl (6). Compound 6 crystallizes in the space group P2₁, [a = 6.888(2), b = 24.771(5), c = 9.105(2) A, β = 111.49(2)°, Z = 2] and shows a high degree of symmetry. In 6 the two α-D-glucopyranosyl residues are in a slightly distorted chair conformation. The glucose moieties are interconnected by a 1,4-dioxane moiety which is in a boat conformation, with the anomeric carbon atoms in the bow positions.