Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1-->4)-C-disaccharides.
Starting from methyl 6-bromo-4,6-dideoxy-alpha-D-threo-4-enopyranoside, 4-C-branched sugars have been prepared through indium-promoted Barbier-type allylation of various aldehydes in aqueous media followed by hydroboration of the resulting double bond. The intermediate unsaturated monosaccharides were shown to rearrange in acidic media to give 4-C-acetyl-5-C-alkyl pyranose compounds. From beta-1-formyl sugars the corresponding beta-(1-->4)-C-disaccharides were obtained.
Levoirier
Eric
E
Laboratoire de Chimie Organique Multifonctionnelle, associé au CNRS (UMR 8614), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud, Bât. 420, F-91405 Orsay, France.
Canac
Yves
Y
Norsikian
Stéphanie
S
Lubineau
André
A
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D007204:Indium / Q000737:chemistry*; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000498:Allyl Compounds; D004187:Disaccharides; D009005:Monosaccharides; D007204:Indium; D014867:Water