685104-40-9

Upstream product

• 685104-19-2 allyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside 
• 685104-39-6 allyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 685104-18-1 allyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->2)-4,6-O-benzylidene-α-D-glucopyranoside 
• 321896-01-9 allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 321896-09-7 allyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside 
• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 685104-21-6 allyl 4-O-acetyl-6-O-triphenylmethyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside 
• 685104-22-7 allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of the trisaccharide and tetrasaccharide moieties of the potent immunoadjuvant QS-21

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.