9386
K. Matsuoka et al. / Tetrahedron Letters 45 (2004) 9383–9386
sialic acid,16 the yield of a glycoside from 14 was unfor-
tunately lower than that from phenyl thioglycoside
(60.7%).
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¨
In conclusion, an efficient synthesis of thiolauryl glyco-
side 2 was accomplished using nonstinking thiol, and
TMSOTf-mediated glycosidation of both anomers was
tested and showed excellent reactivities. Further trans-
formation of thioglycoside 2b into corresponding azido
analogue 14 was performed, and 14 also underwent
TMSOTf-mediated glycosidation to give a known glyco-
side in high yield. This methodology is applicable for
our synthetic studies19 of ÔGlyco-Silicon Functional
MaterialsÕ, including assembly of sialyl lactose19c and
sialyl lactosamine,19d and the results will be reported
in the near future.
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Acknowledgements
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This work was partly supported by a grant from NEDO
[New Energy and Industrial Technology Development
Organization (Glycocluster project)]. We are grateful
to Snow Brand Milk Products Co., Ltd, for providing
the sialic acid used in this study.
17. (a) Schneider, R.; Freyhardt, C. C.; Schmidt, R. R. Eur. J.
Org. Chem. 2001, 1655–1661; (b) Yu, C.-S.; Niikura, K.;
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D.; Kuzuhara, H. Tetrahedron Lett. 1999, 40, 7839–7842;
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D.; Kuzuhara, H. Carbohydr. Res. 2000, 329, 765–772; (c)
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References and notes
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2. For example, see: Hakomori, S.-I.; Igarashi, Y. J.
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3. For example, see: Inoue, Y.; Lee, Y. C.; Troy, F. A., II.
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