English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Tools annual

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools monthly

Global: Zendy Plus monthly

Presents the access of premium content as premium feature

Premium Content

Global: Zendy Plus annual

Global: Zendy Free Plan

The intramolecular aldol condensation of aldohexos-5-ulose derivatives of the D- xylo and L- ribo stereoseries has been studied. Only one of the four possible inososes was isolated from both stereoseries in reasonable yields (30-38%). The results obtained, together with the previous findings for the L- arabino and L- lyxo stereoseries, allowed for the rationalisation of a mechanism of the reaction based on open-transition-state models and electron-withdrawing inductive effects. Complementary reductions of the intermediate inososes were possible by changing the reaction conditions, and two isomeric inositol derivatives were obtained with complete stereoselection from each inosose. The presented approach permits us to control the configuration of three out of the six stereocentres of the inositol frame and gives access to seven of the nine inositols. Noteworthy, for the D- xylo derivative, the two-step sequence (condensation followed by reduction with NaBH(OAc) 3 ) represents the biomimetic synthesis of myo -inositol. Furthermore, the sugar-based pathway leads directly to enantiomerically pure selectively protected inositols and does not require any desymmetrisation procedure which is needed when myo -inositol and other achiral precursors are employed as starting materials. As an example of application of the method, the indirect selective protection of secondary inositols' hydroxy functions, by placing specific protecting groups on the aldohexos-5-ulose precursor has been presented.

Useful access to enantiomerically pure protected inositols from carbohydrates: the aldohexos-5-uloses route