Stereoselective synthesis of alpha-C-Substituted 1,4-dideoxy-1,4-imino-D-galactitols. Toward original UDP-Galf mimics via cross-metathesis.
[reaction: see text] Various alpha-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols were prepared efficiently from 1-O-acetyl-2,3,5,6-tetra-O-benzyl-d-glucofuranose by a four-step sequence involving as the key step the highly syn-selective TMSOTf-catalyzed addition of silylated nucleophiles to a glycofuranosylamine. Cross-metathesis of the alpha-C-allylated iminogalactofuranose derivative with an original uridin-5'-yl vinylphosphonate led to novel UDP-galactofuranose mimics. Such compounds are of interest as potential inhibitors of the mycobacterial galactan biosynthesis pathway.
Liautard
Virginie
V
Institut de Chimie Organique et Analytique, UMR 6005, Université d'Orléans-CNRS Rue de Chartres, BP 6759, F-45067 Orléans Cedex 2, France.
Desvergnes
Valérie
V
Martin
Olivier R
OR
D003500:Cyclization; D004376:Galactitol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D013237:Stereoisomerism; D014531:Uridine Diphosphate Galactose / Q000737:chemistry*
D004376:Galactitol; D014531:Uridine Diphosphate Galactose