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The azidonitration of tri-O-acetyl-D-galactal
Open accessAbstract
Reaction of 3,4,6-tri-O-acetyl-D-galactal with excess ceric ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% β-galacto, 22% α-galacto, and 8% α-talo) and N-acetyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosylamine was formed, on hydrolysis, in 10% yield. The reaction product provides a convenient source of D-galactosamine and 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosylhalides. The crystalline β-chloride is also reported. The use of these glycosyl halides as reactants for the preparation of 2-azido-2-deoxy-α- and -β-D-galactopyranosides under conditions promoted by both mercuric cyanide and silver salts are reported.
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Cited by
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Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Investigating Cellular Metabolism of Synthetic Azidosugars with the Staudinger Ligation
Saxon, E., Luchansky, S. J., Hang, H. C., Yu, C., Lee, S. C., & Bertozzi, C. R. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027748x · Cited by 309
Haurum, J. S., Arsequell, G., Lellouch, A. C., Wong, S. Y., Dwek, R. A., McMichael, A. J., & Elliott, T. (1994) · The Journal of experimental medicine · doi:10.1084/jem.180.2.739 · Cited by 184
Metadata
- Authors
- Lemieux, R. U., & Ratcliffe, R. M.
- Venue
- Canadian Journal of Chemistry
- Publisher
- Canadian Science Publishing
- Published
- 1979-05-15
- Volume
- 57
- Issue
- 10
- Pages
- 1244-1251
- ISSN
- 0008-4042 (ISSN-L)
- 1480-3291
- OpenAlex
- W1964316590
- Cited by
- 651
- References
- 0
- FWCI
- 12.47
- Type
- journal article
- Language
- en
- Open access
- bronze
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