Facile synthesis of per-O-tert-butyldimethylsilyl-beta-D-galactofuranose and efficient glycosylation via the galactofuranosyl iodide.
The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4beta) as a new precursor of D-Gal f units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.
Baldoni
Luciana
L
CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina.
Marino
Carla
C
D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006847:Hydrocarbons, Iodinated; D017646:Organosilicon Compounds; C551677:per-O-tert-butyldimethylsilyl-beta-D-galactofuranose; D005690:Galactose