Efficient Synthesis of O-Linked Glycoconjugates of Amino Acids from Carbohydrate-Derived Donor-Acceptor-Cyclopropanes

Srinivasan Chandrasekaran, Gade Kishore, Vibha Gautam, Shrutisagar Dattatraya Haveli
2019 Heterocycles  
N-Iodosuccinimide (NIS) mediated ring opening of carbohydrate-derived donor-acceptor-cyclopropanes with free "CO2H" group of N-protected L-amino acids at ambient conditions afforded iodo derivatives of glycosyl ester of L-amino acids. The iodides were subsequently converted easily into corresponding azides using NaN3 in DMF followed by reduction with Zn/AcOH to produce ester linked glycosyl amino acids. A similar strategy was adopted to synthesize C-linked glycoamino acid derivatives from
more » ... ent N-protected L-amino alcohols. By using an orthogonal strategy C-and O-linked glycopeptides were also synthesized.
doi:10.3987/com-18-s(f)9 fatcat:yndpsbbvufccvantzdsaovhvo4