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Synlett 2018; 29(02): 148-156
DOI: 10.1055/s-0036-1588582
DOI: 10.1055/s-0036-1588582
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Interrupted Pummerer Reaction in Latent/Active Glycosylation
We thank the National Natural Science Foundation of China (21272082, 21402055, 21672077, 21472054), the State Key Laboratory of Bio-organic and Natural Products Chemistry (SKLBNPC13425), the Natural Science Funds of Hubei Province for Distinguished Young Scholars (2015CFA035), the Wuhan Creative Talent Development Fund, ‘Thousand Talents Program’ Young Investigator Award, and Huazhong University of Science and Technology for support.Further Information
Publication History
Received: 29 July 2017
Accepted after revision: 11 September 2017
Publication Date:
20 October 2017 (online)
In memory of Professor Shuzheng Zhang
Abstract
A latent/active glycosylation strategy is efficient for rapid assembly of oligosaccharides. We recently developed novel OPTB/OPSB and SPTB/SPSB glycosides as two pairs of latent/active glycosyl donors. The active OPSB and SPSB glycosyl donors are efficiently activated by Tf2O via an interrupted Pummerer reaction mechanism. In this account, the design, developments, mechanism studies and applications of these new glycosylation methodologies are described.
1 Introduction
2 Conceiving Ideas
3 Synthesis of OPSB and SPSB Glycosides
4 Substrate Scope
5 Application in the Synthesis of Natural Products
6 Conclusion
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Bz was used as a protecting group instead of Ac to avoid the acyl transfer side reactions: