Carbohydrate Chemistry: Chemical and Biological Approaches, by Rauter A.P. (ed.), Lindhorst T.K. (ed.)

By Rauter A.P. (ed.), Lindhorst T.K. (ed.)

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2007, 342, 1910. 39 J. F. Espinosa, F. J. Can˜ada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt and J. Jimenez-Barbero, J. Am. Chem. , 1996, 118, 10862; G. Rubinstenn, P. Sinay¨ and P. Berthault, J. Phys. Chem. , 1997, 101, 2536. 40 J. F. Espinosa, F. J. Can˜ada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt and J. Jimenez-Barbero, Angew. , Int. , 1996, 35, 303; J. F. Espinosa, E. Montero, J. L. Garcia, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, A.

Thus, 6-mono- and difluoro substituted S-phenyl 2,3,4-tri-Obenzyl-D-mannopyranosides 27 and 28 and the trifluoro analogue of S-phenyl Carbohydr. , 2009, 35, 33–70 | 43 This journal is  c The Royal Society of Chemistry 2009 2,3,4-tri-O-benzyl-a-L-rhamnopyranoside 29 react with 1,2-5,6-di-O-isopropylidene-a-D-glucofuranose 30 to give disaccharides 31–33 in good yield (Scheme 12). The b/a ratio of the disaccharide products increases, going from nonfluorinated substrates to monofluoro donor 27, to difluoro donor 28, and further to trifluoro donor 29.

132 Praly and co-workers133 have developed procedures for the preparation of a-D-C-glycosyl derivatives that use a catalytic amount of Bu3SnCl in the presence of NaBH4 or Bu4NBH3CN in excess as source of hydrogen. Thus, photo-induced radical glycosylation of acrylonitrile or diethyl vinylphosphonate with 148 gives a-C-glucopyranosyl compounds 149 and 150 in 79 and 70% yield, respectively (Scheme 49). Fig. 7 Carbohydr. 135 Stereoselective coupling with 2-substituted acrylates was made possible through the use of pyBox ligand, Zn as the terminal reductant, 2,4-dimethyl-3-pentanol as proton source and dimethylacetamide (DMA) as solvent (Scheme 50).

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