2-(Trimethylsilyl) ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1, 2-trans 1-O-acyl sugars

K Jansson, S Ahlfors, T Frejd, J Kihlberg…

Index: Jansson, Karl; Ahlfors, Stefan; Frejd, Torbjoern; Kihlberg, Jan; Magnusson, Goeran; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 24 p. 5629 - 5647

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Citation Number: 336

Abstract

Twenty-seven mono-tetrasaccharidic 2-(trimethylsilyl) ethyl (TMSET) glycosides were synthesized by the Konigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry. Variously protected TMSET glycosides were treated with BF,. EkO (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55" C, which gave in one step the corresponding protected ...

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