Title: Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose
Authors: Patil, Pratap S.
Lee, Chia-Chen
Huang, Yu-Wen
Zulueta, Medel Manuel L.
Hung, Shang-Cheng
Department of Applied Chemistry
Issue Date: 2013
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 benzylide-nations were developed and later seamlessly utilised as the first transformation in the one-pot procedure.
URI: http://hdl.handle.net/11536/21786
ISSN: 1477-0520
DOI: 10.1039/c3ob40079d
Volume: 11
Issue: 16
Begin Page: 2605
End Page: 2612
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