Abstract
Detailed protocols for the regioselective protection of individual hydroxyls in monosaccharide units are described here. This expedient methodology incorporates up to seven reaction sequences, obviating the necessity to carry out intermittent tedious work-ups and time-consuming purifications. Using this TMSOTf-catalyzed one-pot protocol, the 2,3,4,6-tetra-O-trimethylsilylated hexopyranosides bearing an anomeric group could be transformed into a whole set of differentially protected 2-alcohols, 3-alcohols, 4-alcohols, 6-alcohols and fully protected monosaccharides in high yields. These tailor-made glycosyl donors and acceptors can then be used for stereoselective one-pot glycosylation for oligosaccharide synthesis. The total time for the preparation of a purified protected sugar unit ranges between 1 and 2 d. This process would otherwise take 1–2 weeks.
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Acknowledgements
This work was supported by the National Science Council of Taiwan (NSC 94-2113-M-007-021, NSC 94-2627-M-007-002, NSC 95-2113-M-007-028-MY3, NSC 95-2627-M-007-002 and NSC 95-2752-B-007-002-PAE) and the Academia Sinica (AS-92-TP-A04, 94C007 and AS-95-TP-AB1). S.S.K. thanks Academia Sinica for a postdoctoral fellowship.
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Wang, CC., Kulkarni, S., Lee, JC. et al. Regioselective one-pot protection of glucose. Nat Protoc 3, 97–113 (2008). https://doi.org/10.1038/nprot.2007.493
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DOI: https://doi.org/10.1038/nprot.2007.493
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