Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Ann-Sofie Leppänen, Outi Niittymäki, Kirsti Parikka, Maija Tenkanen, Patrik Eklund, Rainer Sjöholm, Stefan Willför
Förläggare: ELSEVIER SCI LTD
Publiceringsår: 2010
Tidskrift: Carbohydrate Research
Tidskriftsakronym: CARBOHYD RES
Volym: 345
Nummer: 18
Artikelns första sida, sidnummer: 2610
Artikelns sista sida, sidnummer: 2615
Antal sidor: 6
ISSN: 0008-6215


Abstrakt

The C-6 unit of methyl alpha-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 (C) 2010 Elsevier Ltd All rights reserved


Nyckelord

Allylation, Aqueous media, Indium mediated, Methyl alpha-D-galactopyranoside

Senast uppdaterad 2020-14-07 vid 03:54