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