Organic Letters
Letter
(8) (a) Kim, K. S.; Park, J.; Lee, Y. J.; Seo, Y. S. Angew. Chem., Int. Ed.
2003, 42, 459. (b) Fukase, K.; Tanaka, S.-i.; Takashina, M.; Tokimoto,
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17.
are required. The studies outlined herein should motivate the
application of glycosyl bromides in this difficult bond
construction.
ASSOCIATED CONTENT
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S
* Supporting Information
(9) Zhou, M.; O’Doherty, G. A. Org. Lett. 2006, 8, 4339.
Detailed experimental procedures and spectroscopic data for all
new compounds. This material is available free of charge via the
(10) Baryal, K. N.; Adhikari, S.; Zhu, J. J. Org. Chem. 2013, 78, 12469.
(11) (a) Morris, W. J.; Shair, M. D. Org. Lett. 2008, 11, 9. (b) Zhu,
D.; Baryal, K. N.; Adhikari, S.; Zhu, J. J. Am. Chem. Soc. 2014, 136,
3172. For earlier studies of β-glycoside synthesis by anomeric O-
alkylation, see: (c) Box, V. G. S. Heterocycles 1982, 19, 1939.
(d) Schmidt, R. R.; Michel, J. Tetrahedron Lett. 1984, 25, 821.
(e) Schmidt, R. R. Angew. Chem., Int. Ed. 1986, 25, 212. (f) Klotz, W.;
Schmidt, R. R. Liebigs Ann. Chem. 1993, 683.
AUTHOR INFORMATION
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Corresponding Author
Notes
(12) (a) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am.
Chem. Soc. 1988, 110, 8716. (b) Crich, D.; Sun, S.; Brunckova, J. J.
Org. Chem. 1996, 61, 605.
The authors declare no competing financial interest.
(13) Koenigs, W.; Knorr, E. Ber. Dtsch. Chem. Ges. 1901, 34, 957.
(14) For a review of glycosyl halides, see: Nitz, M.; Bundle, D.
Glycosyl Halides in Oligosaccharide Synthesis. In Glycoscience:
Chemistry and Chemical Biology I−III; Fraser-Reid, B., Tatsuta, K.,
Thiem, J., Eds.; Springer: Berlin, Heidelberg, 2001; pp 1497−1542.
(15) (a) Paulsen, H.; Kutschker, W.; Lockhoff, O. Chem. Ber. 1981,
114, 3233. (b) Paulsen, H.; Lockhoff, O. Chem. Ber. 1981, 114, 3102.
(c) Paulsen, H. Angew. Chem., Int. Ed. 1982, 21, 155.
ACKNOWLEDGMENTS
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Financial support from the National Institute of General
Medical Sciences (R01GM090000) is gratefully acknowledged.
We thank Ms. Sandra M. King (Yale University) for assistance
in the preparation of this manuscript.
(16) (a) Binkley, R. W.; Koholic, D. J. J. Org. Chem. 1989, 54, 3577.
(b) Binkley, R. W.; Sivik, M. R. J. Carbohydr. Chem. 1991, 10, 399.
(c) Paterson, I.; McLeod, M. D. Tetrahedron Lett. 1995, 36, 9065.
(d) Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2383.
(e) Crimmins, M. T.; Long, A. Org. Lett. 2005, 7, 4157.
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