130609-18-6

Upstream product

• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 501-53-1 benzyl chloroformate 
• 130539-12-7 N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 130539-13-8 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 130539-15-0 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 130609-19-7 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-galactitol 
• 130539-17-2 4-O-benzoyl-2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-galactitol 
• 130539-14-9 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 130539-16-1 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-4-O-methanesulfonyl-D-glucitol 
• 130539-18-3 2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-galactitol 

Relevant academic research and scientific papers

Selective protection/deprotection in 1-deoxynojirimycin scaffold: Regioselective Mono-Benzoylation and Alkylation using TBAB-NaOH Catalytic System

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-ben-zyloxycarbonyl-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.