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

ABSTRACT: 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

SUBMITTER: D'Andrea F 

PROVIDER: S-EPMC5238563 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature