Orthogonally Protected Cyclohexanehexols by a "One Reaction - One Product" Approach: Efficient Access to Cyclitols and Their Analogs

• Published in: European Journal of Organic Chemistry 2010-05, Vol.2010 (15), p.2945-2953
• Main Authors: Jagdhane, Rajendra C., Shashidhar, Mysore S.
• Format: Article
• Language: English
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Alkylation; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Cyclitols; Exact sciences and technology; Inositol; Organic chemistry; Preparations and properties; Protecting groups; Regioselectivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000009

Differentially protected myo‐inositol derivatives were prepared from commercially available myo‐inositol through regioselective O‐alkylation reactions, which give a single product in each step. These derivatives were converted into six isomeric inositol derivatives carrying orthogonal hydroxy protecting groups. For all these reactions, conditions were chosen to prevent the formation of isomeric products, which obviates the need for separation of isomers and provides the required cyclitol derivative in very good yields. The synthetic potential of these derivatives was illustrated by the conversion of some of the orthogonally protected inositol derivatives into other cyclitol derivatives. Isomeric inositols were also prepared by the global deprotection of all the hydroxy groups. Knowledge of the role of metal ions during the O‐substitution of inositol hydroxy groups paved the way for the efficient preparation of orthogonal (un‐parallel)protected myo‐inositols. Six isomeric inositols and their analogs could be accessed by starting from the differentially protected myo‐inositols I and II.