An Approach to the Synthesis of Four Rhodomicrobium Vannielii Lipid a Analogues
- 1 September 1988
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 7 (3) , 617-644
- https://doi.org/10.1080/07328308808057555
Abstract
The preparation of four Rh. Vannielii Lipid A analogues (i.e. compounds 22, 23, 30 and 33) is described. Non-neighbouring group supported introduction of the β-glycosidic linkages was performed by coupling the mannopyranosyl bromide 2 and the 2-azido-2-deoxy-glucopyranosyl bromides 10 and 13 with the suitably protected glycosyl acceptors 3, 4 and 5 in the presence of a heterogeneous silver catalyst, to give compounds 6, 7, 14 and 24, respectively. Selective removal of the ally1 group and reduction of the azido functions followed by several O,N-acylation steps afforded, after complete deblocking, the tri-and disaccharide Rh. Vannielii Lipid A analogues 22, 23, 30 and 33.This publication has 14 references indexed in Scilit:
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