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By Robert J Ferrier; Royal Society of Chemistry

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Q~-Om2 OH OH 88 86 X = O H 87 X = 0-D-Gkp-S- “D NOS03K HS*NHS02 P-D-GlCP-S-q I 89 NMez OH 90 H 91 The use of thioglycosides in the preparation of 0-glycosides and disaccharides is now well developed as is illustrated in several instances earlier in this Chapter. Very interestingly and importantly, the potential of arylthio groups as leaving groups in glycosylating agents can be affected considerably by substitution in the aromatic rings as illustrated in Scheme 23. That is, electron-donating groups activate leaving potential and, OAc Ar = C,$I4-p-NO2,no reaction; = C&14-p-NHAc or Cd4-p-ONe, rapid reaction Reagents: i, DMTST Scheme 23 conversely, electron-withdrawing groups deactivate.

Lerner, J. Am. Chem. , 1992, 114,4827. T. Tanase, T. Takei, M. Hidai and S . Yano, J. Chem. , 1992, ( S ) 252; (M) 1922. R. Yanagihara, S. Osanai and S . Yoshikawa, Chem. , 1992,89. A. Berger, A. de Raadt. G. Gradnig, M. Grasser, H. L6w and A E . 33,7125. H . Pelmore, G. R. Symons, J. Chem. ,Perkin Trans, 2 , 1992, 149. J. M. Felin, A. Aldaz, J. Clavilier and A. Rodes, J. Electroanal. Chem. , 1991, 316, 175 (Chem. , 1992, 116, 47 933). A. Femandez-Vega, MJ. Llorca and A. Aldaz,NATO ASI Ser. Ser.

1992. 30, 2247 (Chem. , 1992,117, 151 580). A. Moromv. React. Kinet. Cad. 71 (Chem. 174 545). Froma, C. Fuganti, A. Mele, G. PedrOcchi-Fanto~and S. Servi J. Org. 57,999. J. Inanaga. Y. Yokoyama and T. 8109. A. piarulli. Poli, C. Scolastico and R. ViUa, Bull. SOC. Chem. Abstr.. 1991,114,229 241). B. Lacourt-Gadras,M. Grignon-Dubois and B. Rezzonico, Curbohydr. Res.. 1992,235,281. A. D. Schwinden, J. Photochem. photobiol. 241 (Chem. A&. 116. 174 542). A. A. Benner, J. Am. Chem. , 1992,114,6980. Y.

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