Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: A comparative study

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78 Scopus citations

Abstract

Glycosyl iodide donors have been used in both solid- and solution-phase syntheses yielding α-(1→6)-linked glucosyl oligomers in highly efficient protocols. While the solid-phase strategy offers advantages in terms of ease of purification, it requires a total of 7.5 equiv of donor and approximately 12 h to complete the incorporation of one monosaccharide unit. In contrast, solution-phase methods require only 2.5 equiv of donor and 2-3 h reaction time per glycosylation. Moreover, since the reactions are virtually quantitative (>90%) column chromatography of the material is facile. The overall advantages of solution-phase oligosaccharide synthesis were further illustrated in the convergent synthesis of a hexamer (methoxycarbonylmethyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-tetrakis- (2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1→6))-2,3,4-tri-O-benzyl- 1-thio-α-D-glucopyranoside) that was constructed from dimer donor iodides in a two-plus-two and a two-plus-four fashion.

Original languageEnglish (US)
Pages (from-to)1953-1965
Number of pages13
JournalCarbohydrate Research
Volume337
Issue number21-23
DOIs
StatePublished - Nov 19 2002

Keywords

  • α-Linked gluco-homopolymer
  • Glycosyl iodides
  • Oligosaccharide synthesis
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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