Abstract
An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines from the corresponding β-glycosylamines was developed. The procedure is applicable to a wide range of derivatives of monosaccharides (hexoses, 2-acetamido-2-deoxyhexoses, hexuronamides, and 6-deoxyhexoses) and some disaccharides. For the derivatives of pentoses and 2-deoxyhexoses, the use of the corresponding β-glycosylammonium carbamates was found to be more convenient. N-Bromoacetyl-β-glycopyranosylamines derived from D-mannose, L-rhamnose, D-glucuronamide, 2-deoxy-D-arabino-hexose, 2-deoxy-D-lyxo-hexose, and melibiose were obtained for the first time.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. M. Likhosherstov, O. S. Novikova, V. A. Derevitskaya, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1663 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 1512 (Engl. Transl.)].
L. M. Likhosherstov, O. S. Novikova, V. A. Derevitskaya, and N. K. Kochetkov, Carbohydr. Res., 1986, 146, C1.
L. M. Likhosherstov, O. S. Novikova, V. N. Shibaev, and N. K. Kochetkov, Izv. Akad. Nauk, Ser. Khim., 1996, 1848 [Russ. Chem. Bull., 1996, 45, 1760 (Engl. Transl.)].
L. M. Likhosherstov, O. S. Novikova, and V. N. Shibaev, Dokl. Akad. Nauk, 2002, 383, 500 [Dokl. Chem., 2002, 383, 89].
L. M. Likhosherstov, O. S. Novikova, and V. N. Shibaev, Dokl. Akad. Nauk, 2003, 389, 482 [Dokl. Chem., 2003, 389, 73].
L. M. Likhosherstov, O. S. Novikova, and V. N. Shibaev, Izv. Akad. Nauk, Ser. Khim., 1998, 1244 [Russ. Chem. Bull., 1998, 47, 1214 (Engl. Transl.)].
L. M. Likhosherstov, O. S. Novikova, and V. N. Shibaev, Izv. Akad. Nauk, Ser. Khim., 1999, 1377 [Russ. Chem. Bull., 1999, 48, 1365 (Engl. Transl.)].
L. M. Likhosherstov, O. S. Novikova, A. O. Zheltova, and V. N. Shibaev, Izv. Akad. Nauk, Ser. Khim., 2000, 1461 [Russ. Chem. Bull., 2000, 49, 1454 (Engl. Transl.)].
E. W. Thomas, J. Med. Chem., 1970, 13, 755.
E. W. Thomas, Methods Enzymol., 1977, 46, 362.
T. S. Black, L. Kiss, D. Tull, and S. G. Withers, Carbohydr. Res., 1993, 250, 195.
D. Macmillan, A. M. Daines, M. Bayrhuber, and S. L. Flitsch, Org. Lett., 2002, 4, 1467.
L. A. Marcaurelle and C. R. Bertozzi, J. Am. Chem. Soc., 2001, 123, 1587.
B. Paul, R. J. Bernacki, and W. Korytnyk, Carbohydr. Res., 1980, 80, 99.
J. J. Malik and J. M. Risley, Magn. Reson. Chem., 2001, 39, 98.
T. Kiss, A. Erdel, and L. Kiss, Arch. Biochem. Biophys., 2002, 399, 188.
D. J. Vocaldo, J. Wicki, K. Rupitz, and S. G. Withers, Bio-chemistry, 2002, 41, 9736.
J. Chir, S. G. Withers, C. F. Wan, and Y. K. Li, Biochem. J., 2002, 365, 857.
Z. Keresztessy, L. Kiss, and M. A. Hughes, Arch. Biochem. Biophys., 1994, 315, 323.
E. A. Hassoun, D. Bagchi, V. F. Roche, and S. J. Stohs, J. Appl. Toxicol., 1996, 16, 49.
M. F. Ansell and R. H. Gigg, in Rodd's Chemistry of Carbon Compounds, Ed. S. Coffey, Elsevier, Amsterdam, 1965, 1C, 156.
A. C. Rottinger and F. Wenzel, Monatsh. Chem., 1913, 34, 1867.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Likhosherstov, L.M., Novikova, O.S., Zheltova, A.O. et al. An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines, derivatives of mono- and disaccharides. Russian Chemical Bulletin 53, 709–713 (2004). https://doi.org/10.1023/B:RUCB.0000035661.45796.f7
Issue Date:
DOI: https://doi.org/10.1023/B:RUCB.0000035661.45796.f7