Reactivity Controlled by Lattice Interactions in Crystal:  Intermolecular Acyl Transfer in (±)-2,4-Di-O-benzoyl-myo-inositol 1,3,5-Orthoformate

(±)-2,4-Di-O-benzoyl-myo-inositol 1,3,5-orthoformate, on heating in the presence of a base, undergoes transesterification to give 2,4,6-tri-O-benzoyl-myo-inositol 1,3,5-orthoformate and 2-O-benzoyl-myo-inositol 1,3,5-orthoformate in the solid state. The same reaction can also be performed by microwa...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-04, Vol.120 (16), p.3842-3845
Main Authors: Praveen, Thoniyot, Samanta, Uttamkumar, Das, Tanya, Shashidhar, Mysore S, Chakrabarti, Pinak
Format: Article
Language:English
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Summary:(±)-2,4-Di-O-benzoyl-myo-inositol 1,3,5-orthoformate, on heating in the presence of a base, undergoes transesterification to give 2,4,6-tri-O-benzoyl-myo-inositol 1,3,5-orthoformate and 2-O-benzoyl-myo-inositol 1,3,5-orthoformate in the solid state. The same reaction can also be performed by microwave irradiation instead of heating. The crystal structure of the dibenzoate reveals that the screw-axis-related molecules have the hydroxyl and the carbonyl groups ideally oriented for the reaction and gives a close picture of how such a reaction proceeds in enzymes. The structure of the corresponding acetate, (±)-2-O-benzoyl-4-O-acetyl-myo-inositol 1,3,5-orthoformate, lacks this geometry and hence is unreactive in the solid state. Both the acetate and the benzoate undergo base-catalyzed transesterification in solution.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9731332