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ChemComm
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DOI: 10.1039/C8CC05523H
COMMUNICATION
Journal Name
Globally, all these results highlight the advantages of the DBL 12.
reaction in term of regioselectivity and efficiency allowing an
Y. Cen and A. A. Sauve, Nucleosides, Nucleotides and
Nucleic Acids, 2010, 29, 113-122.
13.
N. M. Xavier, A. P. Rauter and Y. Queneau, in
Carbohydrates in Sustainable Development II, eds. A. P.
Rauter, P. Vogel and Y. Queneau, Springer Berlin
Heidelberg, Berlin, Heidelberg, 2010, vol. 295, pp. 19-62.
V. Lemau de Talancé, E. Thiery, G. Eppe, S. E. Bkassiny, J.
Mortier and S. P. Vincent, J. Carbohydr. Chem., 2011, 30,
605-617.
P. Cao, Z.-J. Li, W.-W. Sun, S. Malhotra, Y.-L. Ma, B. Wu
and V. S. Parmar, Natural Products and Bioprospecting,
2015, 5, 37-45.
easy and general access to a broad range of per-benzylated γ-
sugar lactones from their commercial aldoses.
14.
In conclusion, we have developed a new, efficient and
regioselective debenzylative lactonization reaction starting
from per-benzylated acyclic aldoses bearing a carboxylic acid
15.
giving access to various γ-lactone glycosides. This reaction
could be applied to the substrates derived from widely used
commercially available hexoses
(
L
-fucose,
D
-galactose,
D
-
-
16.
17.
18.
S. Enck, P. Tremmel, S. Eckhardt, M. Marsch and A. Geyer,
Tetrahedron, 2012, 68, 7166-7178.
glucose) and pentoses (D-arabinose,
D
-ribose, D
-lyxose,
D
A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P.
Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888-5898.
R. Madsen, in Glycoscience, eds. B. O. Fraser-Reid, K.
Tatsuta and J. Thiem, Springer, Berlin Heidelberg, 2008,
pp. 179-225.
M. Bierenstiel and M. Schlaf, Eur. J. Org. Chem., 2004,
1474-1481.
B. Tang, W. Bi and K. H. Row, Applied Biochemistry and
Biotechnology, 2013, 169, 1056-1068.
xylose), to produce the corresponding γ-lactones in good yields
without the need of a protection/deprotection sequence of
the starting polyol. Furthermore, the findings described herein
represent a significant advance in regioselective synthesis of γ-
lactone glycosides and will create new opportunities for the
generation of original nucleosides and natural compounds.
19.
20.
21.
Conflicts of interest
M. Hrapchak, B. Latli, X.-J. Wang, H. Lee, S. Campbell, J. J.
Song and C. H. Senanayake, J. Labelled Compd.
Radiopharm., 2014, 57, 687-694.
There are no conflicts to declare.
22.
K. Cao, J. A. Brailsford, M. Yao, J. Caceres-Cortes, R. Espina
and S. J. Bonacorsi, J. Labelled Compd. Radiopharm., 2017,
60, 150-159.
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4 | J. Name., 2012, 00, 1-3
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