General methods for. alpha.-or. beta.-O-Ser/Thr glycosides and glycopeptides. Solid-phase synthesis of O-glycosyl cyclic enkephalin analogs

…, L Szabo, J Treiberg, Y Li, VJ Hruby

Index: Polt; Szabo; Treiberg; Li; Hruby Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10249 - 10258

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Citation Number: 133

Abstract

Abstract: 0-Linked glycopeptides have been efficiently synthesized using the highly nucleophilic a-imino esters (O'Donnell's Schiff bases) derived from L-serine (hc), L-threonine (4a, b), and a dipeptide ester (5). General methodology has been developed which can provide 8-glycosides of 8-hydroxy-a-amino acid derivatives 6-16 in excellent yield (63-94%) and excellent selectivity (> 20: 1) using Hanessian's modification or Helferich's ...