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Regioselective one-pot protection of glucose

Nature Protocols volume 3, pages 97–113 (2008)Cite this article

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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Authors and Affiliations

  1. Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan

    Cheng-Chung Wang, Jinq-Chyi Lee, Shun-Yuan Luo & Shang-Cheng Hung

  2. Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei, 115, Taiwan

    Cheng-Chung Wang & Shang-Cheng Hung

  3. Genomics Research Center, Taiwan International Graduate Program, Academia Sinica, Taipei, 115, Taiwan

    Suvarn S Kulkarni & Shang-Cheng Hung

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  1. Cheng-Chung Wang
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Correspondence to Shang-Cheng Hung.

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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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