Carbohydrate Research p. 193 - 200 (1989)
Update date:2022-07-29
Topics:
David, Serge
Malleron, Annie
Dini, Christophe
Di- and tri-saccharides with a 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl unit were prepared by coupling 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (1) to suitably, partially benzylated, acceptor sugar derivatives.Deacetylation followed by acetalation gave 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl derivatives which were treated with N,N'-sulfuryldi-imidazole.The resulting 2-imidazylate group was displaced easily with inversion by benzoate or azide, leading to β-D-mannopyranosyl or 2-azido-2-deoxy-β-D-mannopyranosyl derivatives, respectively.Protected derivatives of β-D-Manp-(1->4)-D-Glc, β-D-Manp-(1->4)-D-Man,β-D-Manp-(1->4)-β-D-Manp-(1->4)-D-Glc, 2-azido-2-deoxy-β-D-Manp-(1->4)-D-Glc, and 2-azido-2-deoxy-β-D-Manp-(1->6)-D-Glc were prepared thus.
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