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Synthesis of oligosaccharides containing the X-antigenic trisaccharide (α-l-Fucp-(1→3)-[β-d-Galp-(1→4)]-β-d-GlcpNAc) at their nonreducing ends

✍ Scribed by Rakesh K. Jain; Khushi L. Matta

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
736 KB
Volume
226
Category
Article
ISSN
0008-6215

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✦ Synopsis

The "armed" methyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside was reacted with "disarmed" phenyl O-(tetra-O-acetyl-beta-D-galactopyranosyl)-(1----4)-6-O-benzyl-2- deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside in the presence of CuBr2-Bu4NBr complex to give phenyl O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1----4)-O- [(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-(1----3])-6-O-benzyl-2-deoxy -2- phthalimido-1-thio-beta-D-glucopyranoside (6) as a novel glycosyl donor. The glycosylating capability of 6 was further examined using N-iodosuccinimide-triflic acid as a reagent. This led to the synthesis of a tetrasaccharide and a pentasaccharide incorporating the X-antigenic structure represented by 6.

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