Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 16, Pages 2605-2612Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40079d
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Funding
- National Science Council [NSC 100-2113-M-001-009-MY3, NSC 101-2628-M-001-006]
- National Health Research Institute [NHRI-EX101-10146NI]
- Academia Sinica
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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.
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