Selective Protection/Deprotection in 1-Deoxynojirimycin Scaffold: Regioselective Mono-Benzoylation and Alkylation using TBAB-NaOH Catalytic System

Iftikhar, M.; Fang, Z.

Acta Chimica Slovenica 65(3): 611-620


ISSN/ISBN: 1580-3155
PMID: 33562910
Accession: 072511086

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Protecting groups play an important role in the carbohydrate chemistry and considerably influence the reactivity of substrate. A study of the substitution of various protecting groups in 1-deoxynojirimycin was carried out. Substrate N-benzyloxycarbonyl- 1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol was subjected to alkylation at positions 2- and 3- to obtain di-substituted products and N-Cbz group was selectively removed by using NaOH in EtOH/H2O. Regioselective benzoylation and alkylation of N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol were conducted under the action of TBAB-NaOH catalytic system. It was found that all protected and mono-protected analogs form simultaneously and their structures were confirmed by spectroscopic means. The results showed that electrophiles play an important role in determining the product distribution.