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The Synthesis of Blood Group Antigenic A Trisaccharide and Its Biotinylated Derivative.

Ekaterina D KazakovaDmitry V YashunskyNikolay E Nifantiev
Published in: Molecules (Basel, Switzerland) (2021)
Blood group antigenic A trisaccharide represents the terminal residue of all A blood group antigens and plays a key role in blood cell recognition and blood group compatibility. Herein, we describe the synthesis of the spacered A trisaccharide by means of an assembly scheme that employs in its most complex step the recently proposed glycosyl donor of the 2-azido-2-deoxy-selenogalactoside type, bearing stereocontrolling 3-O-benzoyl and 4,6-O-(di-tert-butylsilylene)-protecting groups. Its application provided efficient and stereoselective formation of the required α-glycosylation product, which was then deprotected and subjected to spacer biotinylation to give both target products, which are in demand for biochemical studies.
Keyphrases
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