Coupling of glycal derived thioethyl glycosyl donors with glycal acceptors. An advance in the scope of the glycal assembly Journal Article

  


Authors: Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J.
Article Title: Coupling of glycal derived thioethyl glycosyl donors with glycal acceptors. An advance in the scope of the glycal assembly
Abstract: Glycals were converted into thioethyl glycosyl donors through 1,2-anhydrosugar intermediates. Various participating groups in the C-2 position were examined for formation of β-glucosyl, β-galactosyl, and α-mannosyl linkages. A number of disaccharides was prepared employing a novel coupling protocol involving thioethyl 2-pivaloyl glycosyl donors and glycal acceptors. Using this methodology, a linear tetrasaccharide containing exclusively β-glucosyl-(1→4) linkages was prepared in high yields. Ready application to α-mannosylation and C2 branching are other hallmarks of the method.
Keywords: glycosylation; nuclear magnetic resonance spectroscopy; binding site; reaction analysis; x ray diffraction; carbohydrate synthesis; trisaccharide; disaccharide; article
Journal Title: Journal of the American Chemical Society
Volume: 119
Issue: 42
ISSN: 0002-7863
Publisher: American Chemical Society  
Date Published: 1997-10-22
Start Page: 10064
End Page: 10072
Language: English
DOI: 10.1021/ja971640d
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030662091&doi=10.1021%2fja971640d&partnerID=40&md5=caf3e3e3a58ca7d712f61cb3428409e5
Notes: Article -- Export Date: 17 March 2017 -- Source: Scopus
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MSK Authors
  1. Matthias Eckhardt
    3 Eckhardt
  2. Samuel J Danishefsky
    539 Danishefsky
  3. Peter H. Seeberger
    8 Seeberger
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