Enzymatic resolution of racemic 1,2:5,6-di-O-cyclohexylidene and 1,2:3,4-di-O-cyclohexylidene-myo-inositol.
Enzyme-catalyzed regio- and enantioselective esterification of racemic 1,2:5,6-di-O-cyclohexylidene- and 1,2:3,4-di-O-cyclohexylidene-myo-inositol, which are key intermediates for syntheses of various naturally occurring myo-inositol phosphate derivatives, proceeded exclusively in organic solvent to give optically pure materials and selectively protected products in gram scale. Hydrolysis of mono-O-acetates of the corresponding racemic materials catalyzed by the same enzymes yielded complementary products. The present study provides a new and efficient method for obtaining optically pure myo-inositol derivatives.
Ling
L
L
Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, Japan.
Li
X
X
Watanabe
Y
Y
Akiyama
T
T
Ozaki
S
S
D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D004951:Esterification; D006868:Hydrolysis; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
C089355:1,2-3,4-di-O-cyclohexylidene-myo-inositol; C089354:1,2-5,6-di-O-cyclohexylidene-myo-inositol; D012997:Solvents; D007294:Inositol