By Rauter A.P. (ed.), Lindhorst T.K. (ed.)
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Additional resources for Carbohydrate Chemistry: Chemical and Biological Approaches, Vol. 35
2009, 35, 33–70 This journal is c The Royal Society of Chemistry 2009 hemiacetals. Thus, reaction of perbenzylated gluco, manno, galacto and ribo hemiacetals with methyltriphenylphosphonium iodide and BuLi followed by treatment with iodine in THF aﬀorded the 1,2-cis-iodomethylglycosyl compounds with complete or high stereoselectivity (Scheme 26). Scheme 26 1,2-cis-C-Furanosyl compounds generated by iodocyclization of heptenitols. 5 Organometallic addition to aldonolactones Dondoni and Schermann99 have used the addition of 2-lithiothiazole to g-pentonolactones followed by reduction with Et3SiH or (iPr)3SiH/Lewis acid for the synthesis of the sugar aldehyde 80 (Scheme 27).
Chem. Org. Nat. , Springer Verlag, New York, 1985, vol. 48, p. 81; F. Carrel, S. Giraud, O. Spertini and P. Vogel, Helv. Chim. Acta, 2004, 87, 1048; A. Shamshiev, H. J. Gober, A. Donda, Z. Mazora, L. Mori and G. J. E. De Libero, J. Exp. , 2002, 195, 1013; E. Modica, F. Compostella, D. Colombo, L. Franchini, M. Cavallari, L. Mori, G. De Libero, L. Panza and L. F. Ronchetti, Org. , 2006, 8, 3255; P. Wipf and J. G. Pierce, Org. , 2006, 8, 3375; J. Schmied, G. Yang, R. W. Franck and M. Tsuji, J. Exp.
This complex can render the b-anomer by nucleophilic substitution by an alcohol. 29 However, in spite of the fact that good results were obtained by an appropriate choice of reactants and of the reaction conditions, a great deal of attention has been devoted during recent years to the search for successful comprehensive methods for 1,2-cis-glycosylations. They are discussed in the next sections. 4. 1 Methods for the preparation of 1,2-cis-O-glycosides In situ anomerization procedure Lemieux ﬁrst introduced this method30 which is based on the equilibrium established between an a-glycopyranosyl halide and the more reactive b-glycosyl halide catalysed by halide ions derived from tetra-alkylammonium halides.