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A short synthesis of the trisaccharide building block of the N-linked glycans

โœ Scribed by Vadim Y. Dudkin; David Crich

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
147 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An efficient preparation of the core trisaccharide of N-linked glycoproteins containing b-azido functionality at the reducing terminus is described. In the synthesis, triflate-mediated direct b-mannosylation was employed for the formation of the b-D-Man-( 14)-GlcNAc linkage; the anomeric azide installation was achieved through oxazoline ring opening.

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A solution of Id (250mg. 1 mmol: m.p. 79.0-8O.O"C (hexane))[l2] in dry acetonitrile ( 5 mL) was added with a syringe to a nitrogen-purged flask containing [Pd,(dba),].CHCI, (51.8 mg, 0.05 mmol). After stirring for 55 h at room temperature, the reaction mixture was diluted with ether and filtered thr