The first synthesis of secondary sugar sulfonic acids by nucleophilic displacement reactions

András Lipták, Edit Balla, Lóránt Jánossy, Ferenc Sajtos, László Szilágyi

Research output: Article

16 Citations (Scopus)

Abstract

The 4-deoxy-4-C-sulfonic acid and 6-deoxy-6-C-sulfonic acid derivatives of methyl α-D-gluco- and α-D-galactopyranosides were prepared by triflate-mediated nucleophilic displacement reactions, either with NaHSO 3 or with AcSK. The triflate esters of methyl 2,3,4-tri-O-benzyl- 1, methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 9 and methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 5 provided methyl 6-deoxy-6-C-sulfo-α-D-glucopyranoside 4, methyl 4-deoxy-4-C-sulfo-α- D-galactopyranoside 12 and α-D-glucopyranoside 8, respectively. The triflate derivative of methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 13 gave methyl 3,6-anhydro-2,4-di-O-benzyl-α-D-galactopyranoside 14. Formation of the 3,6-anhydro derivative was prevented by using 3,4-O-isopropylidene acetal protection to obtain methyl 6-deoxy-6-C-sulfo- α-D-galactopyranoside 19. The aim of the research is to replace the sulfate esters by sulfonic acids in the repeating oligosaccharide units of glycosaminoglycans or in different oligosaccharide ligands.

Original languageEnglish
Pages (from-to)839-842
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number4
DOIs
Publication statusPublished - jan. 19 2004

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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