Synthesis of model oligosaccharides of biological significance. 3. Synthesis of carbon‐13 labelled trimannosides

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Abstract
Two isomeric trimannosides labelled with carbon‐13 at one specific anomeric position have been synthesized. Methyl 2‐O‐allyl‐4,6‐O‐benzylidene‐α‐D‐mannopyranoside was reacted with tetra‐O‐acetyl‐D‐mannopyranosyl‐1‐13C bromide. The disaccharide obtained was glycosylated with tetra‐O‐acetyl‐D‐mannopyranosyl bromide after hydrolysis of the benzylidene group. This sequence led to methyl 3‐O‐α‐D‐mannopyranosyl‐α‐D‐mannopyranoside after deblocking of all hydroxyl groups. When the 13C‐labelled and unlabelled glycosyl bromides were added to the methyl mannoside in the reversed order, methyl 3‐O‐α‐D‐mannopyranosyl‐6‐O‐α‐D‐mannopyranosyl‐1‐13C‐α.D‐mannopyranoside was obtained.