General access to iminosugar C-glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics.
[reaction: see text] Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.
Godin
Guillaume
G
Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d'Orléans, rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France.
Compain
Philippe
P
Martin
Olivier R
OR
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000475:Alkenes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D000617:Aminoglycosides / Q000138:chemical synthesis*; D002384:Catalysis; D019281:Dimerization; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D018716:Molecular Mimicry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D000498:Allyl Compounds; D000617:Aminoglycosides; D006001:Glycoconjugates; D007097:Imines; D017485:1-Deoxynojirimycin; D012428:Ruthenium; D005944:Glucosamine; C013626:nojirimycin