Abstract
AbstractThe title trisaccharide and tetrasaccharide moieties have been synthesized as part of our research programme to construct the complex triterpenoid saponin QS‐21, a potent immunoadjuvant, which has been used in a series of clinical immunization trials. In view of the unwillingness of glucuronic acid as glycosyl acceptor, the branched glucuronic acid‐containing trisaccharide20was synthesized fromD‐glucose, which was in turn glycosylated at positions 2 and 3, followed by oxidation at position 6, in a linear sequence of 15 steps and in good overall yield. The apiose‐containing tetrasaccharide36was constructed by a linear glycosylation strategy from the non‐reducing terminal sugar,D‐apiose, which was prepared fromD‐xylose by a known procedure, also in a linear sequence of 15 steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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