Electronic versions

  • Emiliano Gemma
    Göteborg University
  • M. Lahmann
    Göteborg University
  • S. Oscarson
    Stockholm University
The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.


  • Calreticulin substrates, Iodide glycosyl donors, Triphenylphosphine oxide promotion, Thioglycoside block donor
Original languageEnglish
Pages (from-to)2558-2562
JournalCarbohydrate Research
Issue number16
Publication statusPublished - 21 Nov 2005
Externally publishedYes
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