Literature DB >> 20845911

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

Thomas J Boltje1, Chunxia Li, Geert-Jan Boons.   

Abstract

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 branched oligosaccharides and their usefulness has been demonstrated by the chemical synthesis of a β-D-Man-(1→4)-D-Man disaccharide, which is appropriately protected for making a range of part-structures of the unusual core region of the lipopolysaccharide of Francisella tularensis.

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Year:  2010        PMID： 20845911      PMCID： PMC2952681          DOI： 10.1021/ol101951u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

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5.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

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6.  Mice vaccinated with the O-antigen of Francisella tularensis LVS lipopolysaccharide conjugated to bovine serum albumin develop varying degrees of protective immunity against systemic or aerosol challenge with virulent type A and type B strains of the pathogen.

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Journal:  Vaccine       Date:  2002-10-04       Impact factor: 3.641

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9.  Regioselective one-pot protection of carbohydrates.

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  5 in total

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Journal:  Chembiochem       Date:  2022-02-11       Impact factor: 3.461

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  5 in total

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