By Robert J Ferrier; Royal Society of Chemistry
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Additional resources for Carbohydrate chemistry : monosaccharides, disaccharides, and specific oligosaccharides, A review of the literature published in 1992
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.
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