Koenigs-Knorr Synthesis

W. Koenigs, E. Knorr, Ber. 34, 957 (1901).

Formation of glycosides from acetylated glycosyl halides and alcohols or phenols in the presence of silver salts. The reaction proceeds with inversion of configuration:

Reviews: Evans et al., Advan. Carbohyd. Chem. 6, 41-52 (1951); K. Igarashi, ibid. 34, 243 (1977); H. M. Flowers, Methods Carbohyd. Chem. 6, 474-480 (1972); R. R. Schmidt, Comp. Org. Syn. 6, 33-64 (1991). Stereoselectivity: J.-I. Tamaru et al., J. Carbohyd. Chem. 12, 893 (1993). Applications: A. Milius et al., New J. Chem. 15, 337 (1991); F. W. Lichtenthaler, T. W. Metz, Tetrahedron Letters 38, 5477 (1997); S. Laszlo et al., Chem. Commun. 1999, 591.