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Org Biomol Chem. 2013 Apr 28;11(16):2605-12. doi: 10.1039/c3ob40079d.

Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose.

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  • 1Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan.

Abstract

Oligosaccharide syntheses are an important source of well-defined sugar constructs particularly needed for the evaluation of structure-activity relationships. The chemical assembly of oligosaccharides requires several building blocks, that is, glycosyl donors and acceptors, which are prepared in multistep processes and in a generally tedious and time-consuming manner. Having developed one-pot procedures meant to minimise the effort in sugar building block preparation, we tackled herein the one-pot preparation of fully protected and 2-, 3-, 4-, and 6-alcohol derivatives of d-mannose, a widely distributed monosaccharide. As a consequence of the hydroxyl group pattern of D-mannose, regioselective and stereoselective benzylidenations were developed and later seamlessly utilised as the first transformation in the one-pot procedure.

PMID:
23446759
[PubMed - indexed for MEDLINE]
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