A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Lipases in the Regioselective Preparation of Glyceric Acid Esters of Methyl Glycosides
Tekijät: Sundell Riku, Kanerva Liisa T
Kustantaja: Wiley-VCH Verlag GmbH & Co. KGaA, Weinham
Julkaisuvuosi: 2013
Journal: European Journal of Organic Chemistry
Lehden akronyymi: EurJOC
Numero: 22
Aloitussivu: 4971
Lopetussivu: 4978
Sivujen määrä: 8
ISSN: 1434-193X
DOI: https://doi.org/10.1002/ejoc.201300450
Tiivistelmä
The lipase-catalyzed regioselective acylation of methyl α-Dgalacto-, -gluco- and -mannopyranosides with isopropylidene-protected (R)- and (S)-glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6-O-mono- and 2,6-O-diacylated products are examined and preparative-scale reactions are detailed. In addition, studies on partially protected methyl α-D-galactopyr-anosides are presented, with the 3,4-O-isopropylidene protected compound leading exclusively to the formation of the
6-O-monoacylated product even at high substrate concentrations. Application of acidic resin in methanol allows removal of the isopropylidene protection groups without disturbing the ester bond at C-6.
The lipase-catalyzed regioselective acylation of methyl α-Dgalacto-, -gluco- and -mannopyranosides with isopropylidene-protected (R)- and (S)-glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6-O-mono- and 2,6-O-diacylated products are examined and preparative-scale reactions are detailed. In addition, studies on partially protected methyl α-D-galactopyr-anosides are presented, with the 3,4-O-isopropylidene protected compound leading exclusively to the formation of the
6-O-monoacylated product even at high substrate concentrations. Application of acidic resin in methanol allows removal of the isopropylidene protection groups without disturbing the ester bond at C-6.
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