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Paper | Special issue | Vol 99, No. 1, 2019, pp.200-212
Published online, 2nd July, 2018
DOI: 10.3987/COM-18-S(F)9
Efficient Synthesis of O-Linked Glycoconjugates of Amino Acids from Carbohydrate-Derived Donor-Acceptor Cyclopropanes

Gade Kishore, Vibha Gautam, Shrutisagar Dattatraya Haveli, and Srinivasan Chandrasekaran*

*Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, India


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 different N-protected L-amino alcohols. By using an orthogonal strategy C- and O-linked glycopeptides were also synthesized.