685104-29-4Relevant articles and documents
Synthesis of the trisaccharide and tetrasaccharide moieties of the potent immunoadjuvant QS-21
Zhu, Xiangming,Yu, Biao,Hui, Yongzheng,Schmidt, Richard R.
, p. 965 - 973 (2007/10/03)
The 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 trisaccharide 20 was synthesized from D-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 tetrasaccharide 36 was constructed by a linear glycosylation strategy from the non-reducing terminal sugar, D-apiose, which was prepared from D-xylose by a known procedure, also in a linear sequence of 15 steps. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.