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
| Autor: | Majid I. Tamboli, Rajesh G. Gonnade, Nivedita Tanaji Patil, Mysore S. Shashidhar |
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| Rok vydání: | 2017 |
| Předmět: |
Resolution (mass spectrometry)
010405 organic chemistry Stereochemistry Chemistry Synthon Diastereomer Crystal growth General Chemistry Crystal structure 010402 general chemistry Condensed Matter Physics 01 natural sciences 0104 chemical sciences law.invention carbohydrates (lipids) chemistry.chemical_compound law lipids (amino acids peptides and proteins) General Materials Science Inositol Crystallization Single crystal |
| Zdroj: | Crystal Growth & Design. 17:5432-5440 |
| ISSN: | 1528-7505 1528-7483 |
| DOI: | 10.1021/acs.cgd.7b00895 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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