Clues from crystal structures pave the way to access chiral myo-inositol derived versatile synthons: resolution of racemic 4-o-allyl-myo-inositol-1,3,5-orthoesters via corresponding dicamphanates by crystallization

TitleClues from crystal structures pave the way to access chiral myo-inositol derived versatile synthons: resolution of racemic 4-o-allyl-myo-inositol-1,3,5-orthoesters via corresponding dicamphanates by crystallization
Publication TypeJournal Article
Year of Publication2017
AuthorsPatil, NT, Shashidhar, MS, Tamboli, MI, Gonnade, RG
JournalCrystal Growth & Design
Volume17
Issue10
Pagination5432-5440
Date PublishedOCT
Type of ArticleArticle
ISSN1528-7483
AbstractRacemic 4-O-allyl-myo-inositol-1,3,5-orthoesters were resolved as the corresponding diastereomeric dicamphanates by crystallization from alcoholic solvents. Crystals of the two diastereomers of myo-inositol orthoacetate and one diastereomer each of myo-inositol orthoformate and myo-inositol orthobenzoate were obtained in >99% purity, on gram scale. The configuration of all these diastereomers was established by conversion to known chiral myo-inositol derivatives as well as by single crystal structure analysis. It is interesting to note that the procedures for the separation of diastereomeric myo-inositol orthoesters could be evolved due to the knowledge of crystal growth and crystal structures of inositol derivatives of comparable molecular structures. Due to the synthetic versatility of myo-inositol orthoesters, the methods described provide rapid and convenient access to a variety of chiral inositol derivatives with high synthetic potential.
DOI10.1021/acs.cgd.7b00895
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.055
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry

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