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Glycosylation with derivatives of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and -α-d-mannopyranosides

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Abstract

Glycosylation of primary (3-trifluoroacetamidopropanol) and secondary (methyl 2,3-O-isopropylidene-α-l-rhamnopyranoside) alcohols with phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-d-glucopyranoside in the presence of N-iodosuccinimide and trimethylsilyl triflate in diethyl ether afforded the corresponding 2-azido-2-deoxyglu-cosides in rather high yields and with good α-stereoselectivity (α:β = 3−5:1). Similar glycosylation with phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-d-manno-pyranoside resulted exclusively in α-linked 2-azido-2-deoxymannosides.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. I. Tokatly, D. Z. Vinnitsky, A. A. Kamneva, D. V. Yashunsky, Y. E. Tsvetkov & N. E. Nifantiev

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  1. A. I. Tokatly
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  2. D. Z. Vinnitsky
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  3. A. A. Kamneva
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  4. D. V. Yashunsky
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  5. Y. E. Tsvetkov
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  6. N. E. Nifantiev
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Corresponding author

Correspondence to N. E. Nifantiev.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-30017).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 785–792, March, 2023.

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Tokatly, A.I., Vinnitsky, D.Z., Kamneva, A.A. et al. Glycosylation with derivatives of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and -α-d-mannopyranosides. Russ Chem Bull 72, 785–792 (2023). https://doi.org/10.1007/s11172-023-3842-6

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  • DOI: https://doi.org/10.1007/s11172-023-3842-6

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