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

• Published in: Crystal growth & design 2017-10, Vol.17 (10), p.5432-5440
• Main Authors: Patil, Nivedita T, Shashidhar, Mysore S, Tamboli, Majid I, Gonnade, Rajesh G
• Format: Article
• Language: English
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/acs.cgd.7b00895

Racemic 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.