On the kinetic resolution of sterically hindered myo-inositol derivatives in organic media by lipases

Sterically hindered myo-inositol derivatives were assayed against different commercial lipases. It was found that dl-1,3,6-tri-O-benzyl-myo-inositol undergoes efficient kinetic resolutions mediated by Pseudomonas sp. lipases (PS-C, PS-IM) and CaLB (Novozym 435). Under the best conditions, the O-acylated l-enantiomorph was obtained in up to >99% ee with conversions of up to >49%. Differences in the immobilization support of the Pseudomonas sp. lipases had a marked effect on their resolution performance.

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l-5-O-Acetyl-1,3,6-tri-O-myo-inositolC29H32O7ee = 99%[α]D25=-24.2 (c 1.36, CHCl3)Source of chirality: kinetic resolution by lipaseAbsolute configuration: (1S,2S,3R,4S,5R,6R)

d-1,3,6-Tri-O-benzyl-myo-inositolC27H30O6ee = 99%[α]D = +17.8 (c 0.45, CHCl3)Source of chirality: kinetic resolution by lipaseAbsolute configuration: (1R,2R,3R,4S,5S,6R)