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A versatile synthesis of the lactoneo-series antigens — synthesis of sialyl dimer Lewis X and of dimer Lewis Y

✍ Scribed by Gerd Hummel; Richard R Schmidt

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
254 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Readily available fucosyl ct(l-3)azidoglucose disaccharide 6 is transformed with galactosyl donors 7 and 8 into Lewis X trisacchadde building blocks 9 and 12, respectively, in high yield. Their suitability for the construction of the lactoneo-series glycosphingolipids is demonstrated. For instance, 9 readily affords glycosyl donor 10 and acceptor 11, which permits the required regioselective 3-O-sialylation of the galactose moiety. Thus, from 11 and 12 hexasaccharide 14 is generated which afforded with lactose acceptor 17 the decisive octasaccharide intermediate 18 which is then transformed either into sialyl dimer Lewis X (1) or into dimeric Lewis Y (2).

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