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Synthesis of model oligosaccharides of biological significance. 3. Synthesis of carbon‐13 labelled trimannosides
Author(s) -
Winnik F. M.,
Carver J. P.,
Krepinsky J. J.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200808
Subject(s) - chemistry , anomer , disaccharide , bromide , hydrolysis , stereochemistry , glycosyl , tetra , glycosyl donor , glycosylation , medicinal chemistry , organic chemistry , biochemistry
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‐ 13 C 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 13 C‐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‐ 13 C‐α.D‐mannopyranoside was obtained.