Organic Letters
Letter
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sequence of 18 steps starting from commercially available tri-O-
acetal glucal. This route is both scalable and the highest yielding
approach to this molecule reported to date by about an order of
magnitude. Central to the success of this approach was the use of
our TsCl-mediated reagent-controlled glycosylation chemistry,
which allowed us to directly construct the β-linked deoxy-sugars
in the landomycin hexasaccharide in a stereoselective fashion
without the need for prosthetic groups. These studies
demonstrate that reagent-controlled approaches hold enormous
promise for streamlining and simplifying oligosaccharide
synthesis.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Experimental details and 1H NMR, 13C NMR, COSY, and
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AUTHOR INFORMATION
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Corresponding Author
ORCID
(33) Nogueira, J. M.; Issa, J. P.; Chu, A.-H. A.; Sisel, J. A.; Schum, R. S.;
Bennett, C. S. Eur. J. Org. Chem. 2012, 2012, 4927−4930.
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Notes
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The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(39) Weber, S.; Zolke, C.; Rohr, J.; Beale, J. M. J. Org. Chem. 1994, 59,
4211−4214.
We thank the National Science Foundation (NSF CHE-
1566233) and National Institutes of Health (R01-GM115779
and U01-GM120414) for generous financial support.
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