Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Tetrahedron letters, 2004-01, Vol.45 (4), p.839-842

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2004

Quelle

Elsevier ScienceDirect Journals

Beschreibungen/Notizen

• Graphic 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.