Schmidt glycosidation

Trichloroacetonitrile reacts with glycosidic hydroxy groups of protected sugars to form glycosyl trichloroacetimidates (R. R. Schmidt, 1980, 1984,1985,1986 B. Wegmann, 1988). The imidate is substituted by alcohols in the presence of trimethylsilyl trifluoromethanesulfonate... 

Pavia H, Cervin G, Lindgren A, Aberg P (1997) Effects of UV-B radiation and simulated herbivory on phlorotannins in the brown alga Ascophyllum nodosum. Mar Ecol Prog Ser 157 139-146 Pawlik JR (1993) Marine invertebrate chemical defenses. Chem Rev 93 1911-1922 Pettit GR, Kamano Y, Herald CL, Tuinman AA, Boettner FE, Kizu H, Schmidt JM, Baczynskyj L, Tomer KB, Bontems RJ (1987) The isolation and structure of a remarkable marine animal antineoplastic constituent dolastatin 10. J Am Chem Soc 109 6883-6885 Pfander H, Stoll H (1991) Terpenoid glycosides. Nat Prod Rep 8 69-95... 

Mahlin, J.A., Jung, K.H., and Schmidt, R.R., Glycosyl imidates, synthesis of flavone C-glycosides vitexin, isovitexin and isoembigenin, Liebigs Ann. Chem., 3, 461, 1995. 

R. R. Schmidt, New methods for the synthesis of glycosides and oligosaccharides. Are there alternatives to the Koenigs-Knorr method Angew. Chem. lnt. Ed. Engl. 25 212 (1986). 

R. R. Schmidt and W. Klotz, Glycoside bond formation via anomeric (7-alkylation How many protective groups are required Synlett p. 168 (1991). W. Klotz and R. R. Schmidt, Anomeric (7-alkylation of (7-unprotected hexoses and pentoses —-convenient synthesis of decyl, benzyl and allyl glycosides, Liebigs Ann. Chem. 683 (1993), and references therein. 

T. MUIIer, R. Schneider, and R. R. Schmidt, Utility of glycosyl phosphites as glycosyl donors— fructofuranosyl and 2-deoxyhexopyranosyl phosphites in glycoside bond fonnation, Tetra-nedron Lett. 35 4763 (1994). 

R. R. Schmidt and J. Michel, Facile synthesis of a- and [3-f7-glycosyl imidates preparation of glycosides and disaccharides, Angew. Chem. Int. Ed. Engl. 79 731 (1980). 

R. R. Schmidt, M. Behrendt, and A. Toepfer, Nitriles as solvents in glycosylation reactions Highly selective (3-glycoside synthesis, Synleti p. 694 (1990). 

R. R. Schmidt and W. Kinzy, Anomeric oxygen activation for glycoside synthesis—the tri-chloroacetimidate method, Adv. Carbohydr. Chem. Biochem. 50 21 (1994), and references cited therein. 

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