Skip to main content
SpringerLink
Log in

Glycosylation with thioglycosides activated by dimethyl(methylthio)sulfonium tetrafluoroborate: synthesis of two trisaccharide glycosides corresponding to the blood group A and B determinants

  • Preliminary Communication
  • Published:
Glycoconjugate Journal Aims and scope Submit manuscript

Abstract

Two trisaccharide glycosides,p-trifluoroacetamidophenylethyl 3-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-2-O-(α-l-fucopyranosyl)-β-d-galactopyranoside andp-trifluoroa-cetamidophenylethyl 2-O-(α-l-fucopyranosyl)-3-O-(α-d-galactopyranosyl)-β-d-galactopyranoside, corresponding to the human blood group A and B determinants, were synthesized. A key fucosylgalactosyl disaccharide derivative was glycosylated with galactosaminyl or galactosyl donors, respectively. Dimethyl (thiomethyl)sulfonium tetrafluoroborate was used for thioglycoside activation in coupling reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Subero C, Jimeno ML, Alemany A, Martin-Lomas M (1984) Carbohydr Res 126:326–30.

    Google Scholar 

  2. Nashed MA, Anderson L (1983) Carbohydr Res 114:43–52.

    Google Scholar 

  3. Bovin NV, Zurabyan SE, Khorlin AY (1983) Carbohydr Res 112:23–35.

    Google Scholar 

  4. Milat M, Sinay P (1981) Carbohydr Res 92:183–89.

    Google Scholar 

  5. Paulsen H, Kolar C (1981) Chem Ber 114:306–21.

    Google Scholar 

  6. David S, Lubineau A, Vatele JM (1980) Nouv J Chem 4:547–58.

    Google Scholar 

  7. Milat ML, Sinay P (1979) Angew Chem 91:501–2.

    Google Scholar 

  8. Auge, C, Veyrieres A (1979) J Chem Soc Perkin 1:1825–32.

    Google Scholar 

  9. Paulsen H, Kolar C (1979) Chem Ber 112:3190–202.

    Google Scholar 

  10. Jaquinet JC, Sinay P (1979) Tetrahedron 35:365–71.

    Google Scholar 

  11. Paulsen H, Kolar C (1978) Angew Chem 90:823–24.

    Google Scholar 

  12. Paulsen H, Kolar C, Stenzel W (1978) Chem Ber 111:2370–75.

    Google Scholar 

  13. Lemieux RU, Driguez H (1975) J Am Chem Soc 97:4069–75.

    Google Scholar 

  14. Kallin E, Lönn H, Norberg T (1988) Glycoconjugate J 5:3–8.

    Google Scholar 

  15. Fügedi P, Garegg PJ, Lönn H, Norberg T Glycoconjugate J (1987) 4:97–108.

    Google Scholar 

  16. Fügedi P, Garegg PJ, (1986) Carbohydr Res 149:c9-c12.

    Google Scholar 

  17. Garegg PJ, Haraldsson M, Lönn H, Norberg T (1988) Glycoconjugate J 4:231–38.

    Google Scholar 

  18. Andersson F, Fügedi P, Garegg PJ, Nashed M (1986) Tetrahedron Lett 27:3919–22.

    Google Scholar 

  19. Meerwein H, Zenner KF, Gipp R (1965) Justus Liebigs Ann Chem 688:67–77.

    Google Scholar 

  20. Nilsson SB, Lönn H, Norberg T (1989) Glycoconjugate J 6:21–34.

    Google Scholar 

  21. Lönn H, Norberg T, Åberg P-M (1988) Glycoconjugate J 5:9–12.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Organic Synthesis Department, BioCarb AB, S-223 70, Lund, Sweden

    Per-Mikael Åberg, Lennart Blomberg, Hans Lönn & Thomas Norberg

Authors
  1. Per-Mikael Åberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lennart Blomberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hans Lönn
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Thomas Norberg
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Åberg, PM., Blomberg, L., Lönn, H. et al. Glycosylation with thioglycosides activated by dimethyl(methylthio)sulfonium tetrafluoroborate: synthesis of two trisaccharide glycosides corresponding to the blood group A and B determinants. Glycoconjugate J 7, 201–205 (1990). https://doi.org/10.1007/BF01050603

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01050603

Key words

Search

Navigation