The Journal of Organic Chemistry 2018-04-13

Tn Antigen Mimics by Ring-Opening of Chiral Cyclic Sulfamidates with Carbohydrate C1-S- and C1-O-Nucleophiles

Pablo Tovillas, Iván García, Paula Oroz, Nuria Mazo, Alberto Avenoza, Francisco Corzana, Gonzalo Jiménez-Osés, Jesús H. Busto, Jesús M. Peregrina

Index: 10.1021/acs.joc.7b03225

Full Text: HTML

Abstract

Starting from commercially available (S)-isoserine and effectively accessible (S)-α-methylserine, enantiopure cyclic sulfamidates have been prepared as chiral building blocks for the synthesis of various S- and O-glycosylated amino acid derivatives, including unnatural variants of the Tn antigen, through highly chemo-, regio-, and stereoselective nucleophilic ring-opening reactions with carbohydrate C1-S- and C1-O-nucleophiles.