Synthesis of N??Glycoside Analogs via Thionolactones

…, P Rattananakin, PG Goekjian

Index: Wang, Wendong; Rattananakin, Pornpun; Goekjian, Peter G. Journal of Carbohydrate Chemistry, 2003 , vol. 22, # 7-8 p. 743 - 751

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Citation Number: 7

Abstract

Indolyl N??glycoside analogs were obtained by a two??step sequence via indole N?? thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N??thioamide. The use of 10: 1 toluene: THF as solvent is important in favoring N??over C 3??acylation. Treatment of the ω??hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N??( ...