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Lipases in the Regioselective Preparation of Glyceric Acid Esters of Methyl Glycosides
Author(s) -
Sundell Riku,
Kanerva Liisa T.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300450
Subject(s) - chemistry , regioselectivity , glyceric acid , acylation , organic chemistry , substrate (aquarium) , methanol , lipase , alcohol , diastereomer , glycoside , catalysis , stereochemistry , enzyme , oceanography , geology
The lipase‐catalyzed regioselective acylation of methyl α‐ D ‐galacto‐, ‐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 ‐galactopyranosides 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.