Synthesis of novel cyclic oligosaccharides: beta-1,6-thio-linked cycloglucopyranosides.
[structure: see text] A protocol for the synthesis of novel cyclic beta-1,6-S-linked glucopyranosides is developed. The key intermediate is a linear thiooligosaccharide bearing an iodo group at C-6 of the nonreducing sugar and a thioacetyl group at the anomeric center of the reducing end sugar. The crucial macrocyclization step was achieved through base-promoted intramolecular S(N)2 glycosylation in remarkably high yields (92-95%) and with well-controlled stereochemistry.
Fan
Linfeng
L
Department of Chemistry, University of Alberta, Edmonton, Canada.
Hindsgaul
Ole
O
D003500:Cyclization; D005697:Galactosides / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
D005697:Galactosides; D009844:Oligosaccharides