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Synthesis 1994; 1994(7): 709-713
DOI: 10.1055/s-1994-25554
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Efficient Synthesis of 2-Deoxyglycosyl-1-O-Acyl Esters via 2-Deoxyglycosyl Phosphorodithioates as Glycosyl Donors

Joanna Borowiecka* , Maria Michalska
  • *Laboratory of Organic Chemistry, Institute of Chemistry, Medical University, Muszynskiego 1, 90-151 Lodz, Poland
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Publication Date:
17 September 2002 (online)

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An efficient glycosylation of carboxylic acids 2a-p has been developed employing 2-deoxyglycosyl phosphorodithioates 1a-h as glycosyl donors and Ag+ salts as activators. In the case of aliphatic acids the method is highly β-stereoselective. Stereoselectivity of glycosylation of aromatic acids depends on their structure. The α/β ratio is temperature dependent. Hydroxy groups in α-hydroxycarboxylic acids are not affected by glycosylation under the reaction conditions used.