Helvetica chimica acta

Synthesis and Some Transformations of 2??Acetamido??5??amino??3, 4, 6??tri??O??benzyl??2, 5??dideoxy??D??glucono??1, 5??lactam

T Granier, A Vasella

Index: Granier, Thierry; Vasella, Andrea Helvetica Chimica Acta, 1998 ,  vol. 81,  # 5  p. 865 - 880

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Citation Number: 40

Abstract

Abstract The lactam 21 was obtained in an overall yield of 72% from the hydroxy amide 16 by oxidation with the Dess-Martin periodinane, acid-catalysed isomerization of the oxidation products in toluene, whereupon 18/19 precipitated, and reductive dehydroxylation of 18/19 (Et 3 SiH/BF 3· OEt 2; Scheme 1). The amide 16 was obtained by ammonolysis of the N- acetylglucosamine-derived lactone 15. Depending on the oxidation method, 16 yielded ...