Taming of the DIBAL Promoted Debenzylation of α-Cyclodextrin. Kinetics, Substituent Effects and Efficient Synthesis of Lings Tetrol.

ABSTRACT: The kinetics of the reaction of perbenzyl α-cyclodextrin was studied varying the concentration of DIBAL and substrate, and the temperature. The initial debenzylation was found to be 1^st order in substrate and follow the relationship 0.0675+0.179[DIBAL]² with respect to the concentration of DIBAL. The second and the third debenzylation which led to the 3^A ,6^A ,6^D -triol (Lings triol) were both found to be 1^st order in substrate concentration and zero order in DIBAL concentration. Longer reaction times with DIBAL in high concentration gave further debenzylation to comparatively complex mixtures containing the 2B,3^A ,6^A ,6^D -tetrol and the 3^A ,6^A ,6^C ,6^D

SUBMITTER: Bols M 

PROVIDER: S-EPMC9325365 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature