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¨
anomeric azide group was reduced with LiAlH4 followed by
protection of the resulting amine as N-nosyl group to give 41
which was cyclized to the piperidine derivative 42 under the
Mitsunobu conditions. Deprotections of the nosyl, benzyl and
the MOM groups led to the formation of the piperidine 44, an
iminosugar as a potential glycosidase inhibitor.28
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Conclusions
In conclusion, we have shown that the reagent system PIFA–
Me3SiN3 in presence of TMSOTf as a catalyst conveniently
converts glycals into the corresponding 1,2-diazido derivatives.
These vicinal azido derivatives are converted to 2-azido-N-
glycopeptides, which are convenient precursors of 2-amino-N-
glycopeptides, and also into a pseudotrisaccharide 15. Likewise,
glycals are converted into a mixture of 1-azido-2-acetoxy sugars
and 2-azido-1-acetoxy sugars using the reagent system PIDA–
Me3SiN3 in the presence of TMSOTf as a catalyst. The –OAc
group of 2-azido-1-acetates can be hydrolyzed and converted
into a trichloroacetimidate group for effecting glycosylations.
One of the azidoacetates 3 was converted into a pseudo-
trisaccharide 38 aer glycosylation followed by click chemistry.
Further, 1-azido-2-acetoxy sugar derivative 29, derived from the
arabinal derivative 10b, was eventually converted into a piperi-
dine triol 44, a potential glycosidase inhibitor. Tentative
mechanisms have been proposed to account for the formation
of different azido sugars.
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There are no conicts to declare.
Acknowledgements
We thank the Department of Science and Technology, New
Delhi, India, for a J. C. Bose National Fellowship (No. SR/S2/JCB-
26/2010) to Y. D. V. A. C. thanks the Council of Scientic and
Industrial Research, New Delhi for
Fellowship.
a Senior Research
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