Structure-taste relationships among cyclic glycols, levoglucosan, and methyl glycopyranosides

An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S,3R)-3-(acetoxy)-1-cyclohexanol ((R,S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's up to >99.5%). (R,R)-Diacetate ((R,R)-3a) was obtained in a DYKAT process at room temperature from (1S,3R)-3-acetoxy-1-cyclohexanol ((R,S)-2a), in a high trans/cis ratio (91:9) and in excellent enantioselectivity of >99%. Metal- and enzyme-catalyzed dynamic transformation of cis/trans-1,3-cyclohexanediol using PS-C gave a high diastereoselectivity for cis-diacetate (cis/trans = 97:3). The (1R,3S)-3-acetoxy-1-cyclohexanol (ent-(R,S)-2a) was obtained from cis-diacetate by CALB-catalyzed hydrolysis in an excellent yield (97%) and selectivity (>99% ee). By deuterium labeling it was shown that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

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Structure-taste relationships among cyclic glycols, levoglucosan, and methyl glycopyranosides

Cited by 4 publications

References 5 publications

Amine-catalyzed transformation of enolic nonenzymic browning products, isomaltol glycopyranosides into 1,6-anhydro-β-d-hexopyranoses

Amine-catalyzed transformation of enolic nonenzymic browning products, isomaltol glycopyranosides into 1,6-anhydro-β-d-hexopyranoses

The Chemistry and Biochemistry of the Sweetness of Sugars

Enzymatic Resolution, Desymmetrization, and Dynamic Kinetic Asymmetric Transformation of 1,3-Cycloalkanediols

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