An Efficient Synthesis of the Lewis A (Lea) Antigen Pentasaccharide Moiety
- 1 October 1993
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 12 (7) , 809-822
- https://doi.org/10.1080/07328309308020096
Abstract
Starting material for the synthesis of Lewis A pentasaccharide (1) was azidoglucose derivative 2 which was readily transformed into the 3,4-O-unprotected derivative 3 or the 3-O-unprotected derivative 5, respectively. Reaction of 3 and O-galactosyltrichloroacetimidate 6 led preferentially to the desired β(1-3)-connected disaccharide 8 which could be selectively obtained from donor 6 and acceptor 5 via disaccharide 9. 4a-O-Fucosylation of 8 with fucosyl donor 10 furnished trisaccharide 11 which was transformed into triosyl donor 13; glycosylation of lactose derivative 14 as acceptor furnished the desired pentasaccharide in high yield. Azide reduction and N-acetylation and O-deprotection afforded the title compound 1 in high overall yield.Keywords
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