1250346-68-9

Upstream product

• 1250346-57-6 allyl 4,6-di-O-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1-4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranoside 

Downstream Products

• 1392224-75-7 allyl 3,4,6-tri-O-acetyl-2-O-[((S)-2-phenylthiomethyl)benzyl]-α-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-O-diethylisopropylsilyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Chemical synthesis and immunological evaluation of the inner core oligosaccharide of francisella tularensis

Francisella tularensis, which is a Gram negative bacterium that causes tularemia, has been classified by the Center for Disease Control and Prevention (CDC) as a category A bioweapon. The development of vaccines, immunotherapeutics, and diagnostics for F. tularensis requires a detailed knowledge of the saccharide structures that can be recognized by protective antibodies. We have synthesized the inner core region of the lipopolysaccharide (LPS) of F. tularensis to probe antigenic responses elicited by a live and subunit vaccine. The successful preparation of the target compound relied on the use of a disaccharide which was modified by the orthogonal protecting groups diethylisopropylsilyl (DEIPS), 2-naphthylmethyl (Nap), allyl ether (All), and levulinoyl (Lev) ester. The ability to remove the protecting groups in different orders made it possible to establish the optimal glycosylations sequence to prepare a highly crowded 1,2,3-cis configured branching point. A variety of different methods were exploited to control anomeric selectivities of the glycosylations. A comparison of the 1H NMR spectra of isolated material and the synthetic derivative confirmed the reported structural assignment of the inner core oligosaccharide of F. tularensis. The observation that immunizations with LPS lead to antibody responses to the inner core saccharides provides an impetus to further explore this compound as a vaccine candidate.

Versatile set of orthogonal protecting groups for the preparation of highly branched oligosaccharides

A new set of orthogonal protecting groups has been developed based on the use of a diethylisopropylsilyl (DEIPS), methylnaphthyl (Nap), allyl ether, and levulinoyl (Lev) ester. The protecting groups are ideally suited for the preparation of highly branche