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As part of an ongoing project aimed at identifying protective capsular polysaccharide epitopes for the development of vaccine candidates against the fungal pathogen  Cryptococcus neoformans , the synthesis and glycosylation properties of a naphthalenylmethyl (NAP) orthogonally protected trisaccharide thioglycoside, a common building block for construction of serotype B and C capsular polysaccharide structures, were investigated. Ethyl (benzyl 2,3,4‐tri‐ O ‐benzyl‐β‐ d ‐glucopyranosyl‐ uronate)‐(1→2)‐[2,3,4‐tri‐ O ‐benzyl‐β‐ d ‐xylopyranosyl‐(1→4)]‐6‐ O ‐benzyl‐3‐ O ‐(2‐naphthalenylmethyl)‐1‐thio‐α‐ d ‐mannopyranoside was prepared and used both as a donor and an acceptor in glycosylation reactions to obtain spacer equipped hexa‐ and heptasaccharide structures suitable either for continued elongation or for deprotection and printing onto a glycan array or conjugation to a carrier protein. The glycosylation reactions proceeded with high yields and α‐selectivity, proving the viability of the building block approach also for construction of 4‐ O ‐xylosyl‐containing  C. neoformans  CPS structures.

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Synthesis of a Glucuronic Acid‐Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of  Cryptococcus Neoformans  Capsular Polysaccharide Fragments