Metal-mediated allylation of enzymatically oxidized methyl α-D-galactopyranoside.
The C-6 unit of methyl α-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction. The Barbier-Grignard type reaction, where a carbonyl group reacts with an allyl halide, proceeds in aqueous solution, even with water as the only solvent; thus carbohydrates can be modified without the need for drying or protection-deprotection steps. The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride. The main products were isolated and characterized by GC-MS and NMR spectroscopy.
Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, FIN-20500 Turku, Finland. aleppane@abo.fi
Ann-Sofie
AS
Leppänen
Outi
O
Niittymäki
Kirsti
K
Parikka
Maija
M
Tenkanen
Patrik
P
Eklund
Rainer
R
Sjöholm
Stefan
S
Willför
D000498:Allyl Compounds / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D007204:Indium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000498:Allyl Compounds; C469243:methyl-galactopyranoside; D007204:Indium; C050431:allyl bromide; D005690:Galactose