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
| Title | 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 |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Patil, NT, Shashidhar, MS, Tamboli, MI, Gonnade, RG |
| Journal | Crystal Growth & Design |
| Volume | 17 |
| Issue | 10 |
| Pagination | 5432-5440 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 1528-7483 |
| Abstract | 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. |
| DOI | 10.1021/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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