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1 Polish Journal of Chemistry

1 1999

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Efficient synthesis of lactoneo series antigen lewis Y (LeY)

Hummel G., Schmidt R.

Polish Journal of Chemistry

1999

vol. 73 nr 6

941-954

The synthesis of glycosphingolipid Lewis Y (1) could be efficiently carried out, based on the connection of building blocks 2-7. Reaction of fucosyl donor 2 with azidoglucose derivative 4 as acceptor gave a(1-3)-linked disaccharide 8, which was transformed to acceptor 9; ensuing reaction with galactosyl donor 3 furnished Lewis X trisaccharide derivative 10. This compound could be transformed into the LeY hexasaccharide 16 either via transformation into glycosyl donor 12, connection with lactose moiety 5, and then reaction with fucosyl donor 2a, or, alternatively by transformation of 10 into acceptor 18, reaction with fucosyl donor 2, and then attachments of lactose moiety 5. Application ot the azidosphingosine glycosylation procedure to 16, i.e. first transformation into O-acyl protected hexaosyl donor 33, then reaction eith azidosphingosine 6 and fatty acid (7), and finally O-acyl deprotection, afforded target molecule 1 in high purity.