Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.

@article{Winnik1982SynthesesOM,
  title={Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.},
  author={F M Winnik and J. R. Brisson and Jeremy Carver and J. J. Krepinsky},
  journal={Carbohydrate research},
  year={1982},
  volume={103 1},
  pages={15-28}
}
Methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl) -alpha-D-mannopyranoside (12) was prepared in 90% yield by Helferich glycosylation of methyl 2-O-allyl-4,6-O-benzylidene-alpha-D-mannopyranoside (9) with tetra-O-acetyl-alpha-D-mannopyranosyl bromide (11). Removal of the benzylidene group and second Helferich glycosylation with 11 led to methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (14) which, after… CONTINUE READING