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Synlett 2017; 28(10): 1121-1126
DOI: 10.1055/s-0036-1588722
DOI: 10.1055/s-0036-1588722
synpacts
2,6-Lactones as a New Entry in Stereoselective Glycosylations
Further Information
Publication History
Received: 27 December 2016
Accepted after revision: 24 January 2017
Publication Date:
23 February 2017 (online)
Abstract
The advantages of glycosyl donors bearing a 2,6-lactone moiety in 1,2-cis-β-glycosylation reactions are discussed in the context of recent comprehension on the SN2–SN1 borderline. The 2,6-lactone structure increases the likelihood of the SN2-like reaction, analogous to 4,6-tethered structures or 2-O-electron-deficient substituents, which are known to mound the energetic barrier to SN1 reactions. Furthermore, the glycosyl cation generated from the 2,6-lactone donor seems to direct β-glycosides similar to the torsional and flipped cations generated from 4,6-tethered donors and mannuronate or 3,6-lactone donors, respectively. Overall, 2,6-lactones are suitable for use in 1,2-cis-β-glycosylations, and this novel class of donors is expected to help deepen our global understanding of glycosylation reactions.
1 Introduction
2 Stereoinversion (SN2-Like) Reactions
3 Conformational Control of Glycosyl Cations
4 Conclusions
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